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1,2-Bis(Hetaryl)Perfluorocyclopentenes as Unique Thermally Irreversible Photochromes. Synthesis and Structural Singularities

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Fluorine in Heterocyclic Chemistry Volume 1

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Abstract

The review considers the synthesis and structures of photochromic products, in which hetaryl substituents are separated by the central 1,2-perfluorocyclopentene moiety. It was also briefly presented main methods for synthesis of octafluorocyclopentene and its reactivity. Among methods used for the synthesis of the photochromes, the reactions of lithium derivatives of thiophene, benzothiophene, and other heterocyclic compounds with octafluorocyclopentene, 1,2-dichlorohexafluorocyclopentene, and their analogues are described. Another general method for the synthesis of dihetarylethenes, considered in the review, is based on the McMurry reaction involving the initial synthesis of 1,5-diketone by acylation of the corresponding heterocyclic compound with perfluoroglutaryl dichloride followed by the cyclization of the diketone in the presence of metallic titanium or its salts. The review also summarizes the results of X-ray diffraction studies of some 1,2-dihetarylperfluorocyclopentenes.

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References

  1. Irie M, Mohri M (1988) Thermally irreversible photochromic systems. Reversible photocyclization of diarylethene derivatives. J Org Chem 53:803–808. doi:10.1021/jo00239a022

    Article  CAS  Google Scholar 

  2. Irie M (1989) Advances in photochromic materials for optical data storage media. Jpn J Appl Phys 28(Suppl 28–3):215–219

    Article  CAS  Google Scholar 

  3. Irie M (1994) Photo-reactive materials for ultrahigh density optical memory. Elsevier, Amsterdam

    Google Scholar 

  4. Irie M (2000) Diarylethenes for memories and switches. Сhem Rev 100:1685–1716. doi:10.1021/cr980069d

    CAS  Google Scholar 

  5. Krayushkin MM (2001) Synthesis of photochromic dihetarylethenes. Khim Geterotsikl Soedin 19–40

    Google Scholar 

  6. Kobatake S, Irie M (2003) Photochromism. Annu Rep Prog Chem Sect C 99:277–313. doi:10.1039/b208508a

    Article  CAS  Google Scholar 

  7. Tian H, Yang S (2004) Recent progresses on diarylethene based photochromic switches. Chem Soc Rev 33:85–97. doi:10.1039/b302356g

    Article  CAS  Google Scholar 

  8. Krayushkin MM, Barachevsky VA, Irie M (2007) Synthesis of thienyl-containing photochromes (dithienylethenes, fulgides, fulgimides, and spirocompounds). Heteroatom Chem 18:557–567. doi:10.1002/hc.20334

    Article  CAS  Google Scholar 

  9. Irie M (2008) Photochromism and molecular mechanical devices. Bull Chem Soc Jpn 81:917–926. doi:10.1246/bcsj.81.917

    Article  CAS  Google Scholar 

  10. Barachevsky VA, Krayushkin MM (2008) Photochromic organic compounds for optical memory. Russ Chem Bull Int Ed Engl 57:867–875

    Article  CAS  Google Scholar 

  11. Cusido J, Deniz E, Raymo FM (2009) Fluorescent switches based on photochromic compounds. Eur J Org Chem 2009:2031–2045. doi:10.1002/ejoc.200801244

  12. Irie M (2010) Photochromism of diarylethene molecules and crystals. Proc Jpn Acad Ser B 86:472–483. doi:10.2183/pjab.86.472

    Article  CAS  Google Scholar 

  13. Bertarelli C, Bianco A, Castagna R, Pariani G (2011) Photochromism into optics: opportunities to develop a light-triggered optical elements. J Photochem Photobiol C: Photochem Rev 12:106–125. doi:10.1016/j.jphotochemrev. 2011.05.003

    Article  CAS  Google Scholar 

  14. Parthenopoulos DA, Rentzepis PM (1989) Three-dimensional optical storage memory. Science 245:843. doi:10.1126/science.245.4920.843

    Article  CAS  Google Scholar 

  15. Irie M, Matsuda K (2001) Memories. In: Balzani V (ed) Electron transfer in chemistry. Springer, Berlin, pp 215–242

    Chapter  Google Scholar 

  16. Irie M (2001) Photoswitchable molecular systems based on diarylethenes. In: Feringa BL (ed) Molecular switches. Wiley, Weinheim, pp 37–62

    Google Scholar 

  17. Bianco A, Bertarelli C, Dassa G, Toso G, Zerbi G (2008) Realization of photochromic polymeric films for optical applications. Adv Sci Technol 55:1–6

    Article  CAS  Google Scholar 

  18. Corns SN, Partington SM, Towns AD (2009) Industrial organic photochromic dyes. Color Technol 125:249–261. doi:10.1111/j.1478-4408.2009.00204.x

    Article  CAS  Google Scholar 

  19. Han M, Lee S, Jung J, Park KM, Kwon SK, Ko J, Lee PH, Kanga Y (2006) Effect of a perfluorocyclopentene core unit on the structures and photoluminescence of fluorene- and anthracene-based compounds. Tetrahedron 62:9769–9777. doi:10.1016/j.tet.2006.07.065

    Article  CAS  Google Scholar 

  20. Berberich M, Natali M, Spenst P, Chiorboli C, Scandola F, Würthner F (2012) Nondestructive photoluminescence read-out by intramolecular electron transfer in a perylene bisimide-diarylethene dyad. Chem Eur J 18:13651–13664. doi:10.1002/chem.201201484

    Article  CAS  Google Scholar 

  21. Heitzman RJ, Patrick CR, Stephens R, Tatlow JC (1963) 45. Fluorocyclopentanes. Part I. The 1H,2H- and 1H,3H-octafuorocyclopentanes, and 1H,3H/2H-heptafluorocyclopentane. J Chem Soc 1963:281–289. doi:10.1039/JR9630000281

    Article  Google Scholar 

  22. Henne AL, Latif KA (1954) Perfluorinated alkene, alkyne and cycloalkene. J Am Chem Soc 76:610–612. doi:10.1021/ja01631a089

    Article  CAS  Google Scholar 

  23. Maynard JT (1963) The synthesis of highly fluorinated compounds by use of potassium fluoride in polar solvents. J Org Chem 28:112–115. doi:10.1021/jo01036a025

    Article  CAS  Google Scholar 

  24. Henne AL (1962) Replacing vinylic halogens with fluorine. US 3024290, CA 56:15333i

    Google Scholar 

  25. Sekiya A, Yamada T, Watanabe K (1998) Process for producing fluorinated alkene and fluorinated alkane. US 005847243A

    Google Scholar 

  26. Ji HS, Cho OJ, Ryu JG, Yang JY, Ahn YH, Kim BS, Kim DH (2007) Octafluorocyclopentene as dry etching gas for semiconductor devices manufacturing. DE 102006049156

    Google Scholar 

  27. Mase T, Kim YN, Yamada T (2001) Preparation of 1,2,3,3,4,4,5,5- octafluorocyclopentene. JP 2001247493A

    Google Scholar 

  28. Ozol SI, Vinogradov DV, Mikhailov IN, Zaitsev S, Barabanov VG (2008) Process for preparation of octafluorocyclopentene by fluorination of mixed chloro- and fluoro-containing cyclopentenes with potassium fluoride in DMF containing a small amount of water. RU 2318793

    Google Scholar 

  29. Otsuki N (2005) Environmentally friendly new five-member-ring fluoro compound manufacture and their practical application. Petrotech 28:489–493

    CAS  Google Scholar 

  30. Yamada T, Otsuki N, Sugimoto T, Tanaka K, Sekiya A (2003) Preparation technology and properties of environmentally friendly five-membered cyclic fluoro compounds. Fain Kemikaru 32:13–20

    CAS  Google Scholar 

  31. Yamada T, Sekiya A (1998) Development of next-generation fluorine compounds. Eco Industry 3:31–39

    CAS  Google Scholar 

  32. Yamada S, Ishii E, Konno T, Ishihara T (2008) Preparation of perfluorocyclopentenylmetal species and their cross-coupling reaction with electrophiles – remarkable accesses to versatile perfluorocyclopentene derivatives. Tetrahedron 64: 4215–4223 (p 4222 and references cited therein). doi:10.1016/j.tet.2008.02.089

  33. Clayton AB, Roylance J, Sayers DR, Stephens R, Tatlow JC (1965) Polyfuorocycloalkenes. Part III. Reactions with alcohols under ionic conditions to give ethers. J Chem Soc 7358–7367. doi:10.1039/JR9650007358

  34. Lindner PE, Lemal DM (1996) Highly fluorinated cyclopentanones and their enols. J Org Chem 61:5109–5115. doi:10.1021/jo9602940

    Article  CAS  Google Scholar 

  35. Stockel RF, Beachem MT, Megson FH (1964) The reaction of methoxide ion with perfluorocyclopentene. Can J Chem 42:2880–2883. doi:10.1139/v64-425

    Article  CAS  Google Scholar 

  36. Cracowski JM, Sharma B, Brown DK, Christensen K, Lund B, Smith DW Jr (2012) Perfluorocyclopentenyl (PFCP) aryl ether polymers via polycondensation of octafluorocyclopentene with bisphenols. Macromolecules 45:766–771. doi:org/10.1021/ma2024599

    Article  CAS  Google Scholar 

  37. Yamada S, Ishii E, Konno T, Ishihara T (2007) Reaction of perfluorocyclopentene with various carbon nucleophiles – heteroaromatic lithium reagents, enolate and phosphonium ylide. Org Biomol Chem 5:1442–1449. doi:10.1039/B701702B

    Article  CAS  Google Scholar 

  38. McBee ET, Turner JJ, Morton CJ, Stefani AP (1965) Reaction of amines with cyclic fluorinated olefins. J Org Chem 30:3698–3705. doi:10.1021/jo01022a025

    Article  CAS  Google Scholar 

  39. Mir Q, Shreeve JM (1994) Reactions of 1, 2-dichlorotetrafluorocyclobut-1-ene and 1, 2-dichlorohexafluorocyclopent-1-ene with 2-mercaptoethanol and ethanedithiol and of their products. J Fluorine Chem 68:269–272. doi:10.1016/0022-1139(93)05006-M

    Article  CAS  Google Scholar 

  40. Bayliff AE, Bryce MR, Chambers RD (1987) Polyhalogenoheterocyclic compounds. Part 38 reactions of fluorinated alkenes and cycloalkenes with difunctional nucleophiles. J Chem Soc Perkin I 763–767. doi:10.1039/P19870000763

  41. Yamada S, Konno T, Ishihara T, Yamanaka H (2005) Reaction of octafluorocyclopentene with various carbon nucleophiles. J Fluorine Chem 126:125–133. doi:10.1016/j.jfluchem.2004.10.047

    Article  CAS  Google Scholar 

  42. Chambers RD, Kirk JR, Powell RL (1983) Polyhalogenoheterocyclic compounds. Part 35. Reactions of fluorinated alkenes and cycloalkenes with enolate anions. J Chem Soc Perkin I 1983:1239–1242. doi:10.1039/P19830001239

    Article  Google Scholar 

  43. Krayushkin MM, Kalik МA, Dzhavadov DL (1998) Synthesis, structure and some reactions of 1,2-bis(2-alkylthio-3-thienyl) perfluorocyclopentene. Khim Geterotsikl Soedin 927–933

    Google Scholar 

  44. Krayushkin MM, Kalik МA, Dzhavadov DL, Martynkin AYu, Firsov AV, Uzhinov BM (1999) Photochromic diarylethenes. 2. Synthesis and photochromic properties of 5,5′ alkylthio(alkylsulfonyl)-substituted 1,2-bis(2-alkylthien-3-yl) perfluorocyclopentenes. Izv Acad Nauk Ser Khim 979–982

    Google Scholar 

  45. Krayushkin MM, Uzhinov BM, Martynkin AY, Dzhavadov DL, Kalik МA, Ivanov VL, Stoyanovich FM, Uzhinova LD, Zolotarskaya OY (1999) Thermally irreversible photochromic diarylethenes. Int J Photoenergy 1:183–190

    Article  CAS  Google Scholar 

  46. Krayushkin MM, Stoyanovich FM, Zolotarskaya OYu, Martynkin AYu, Ivanov VL, Uzhinov BM (1999) Photochromic dihеtarylethenes. 3. Synthesis and photochromic properties of 1, 2-bis[2-methyl-(5-benzoxazol-2-yl)thien-3-yl] hexafluorocyclopentene. Izv Acad Nauk Ser Khim 1011–1013

    Google Scholar 

  47. Krayushkin MM, Stoyanovich FM, Zolotarskaya OY, Murav’ev IV, Martynkin AY, Uzhinov BM (2001) Photochromic dihеtarylethenes.10 Photochromic 1,2-bis[2-benzothiazol-2-yl-3-thienyl] and 1,2-bis[2-benzothiazol-2-yl)benzothiophen-3-yl]ethenes. Russ Chem Bull Int Ed Engl 50:2420–2423

    Article  CAS  Google Scholar 

  48. Kawai SH, Gilat SL, Lehn J-M (1999) Photochemical pKa-modulation and gated photochromic properties of a novel diarylethene switch. Eur J Org Chem 1999:2359–2366. doi:10.1002/(SICI)1099-0690(199909)1999:9<2359

  49. Takeshita M, Irie M (1998) Reversible fluorescence intensity change of a diarylethene. Chem Lett: 1123–1124

    Google Scholar 

  50. Yang T, Pu S, Fan C, Liu G (2008) Synthesis, crystal structure and optoelectronic properties of a new unsymmetrical photochromic diarylethene. Spectrochim Acta Part A 70:1065–1072. doi:org/10.1016/j.saa.2007.10.026

    Article  Google Scholar 

  51. Uchida K, Irie M (1995) A photochromic dithienylethene that turns yellow by UV irradiation. Chem Lett 969–970. doi:org/10.1246/cl.1995.969

    Google Scholar 

  52. Yamaguchi T, Fujita Y, Irie M (2004) Photochromism of a novel 6π conjugate system having a bis(2,3′-benzothienyl) unit. Chem Commun 1010–1011. doi:10.1039/B401207K

  53. Frigoli M, Mehl H (2005) Multiple addressing in a hybrid biphotochromic system. Angew Chem Int Ed Engl 44:5048–5052. doi:10.1002/anie.200462575

    Article  CAS  Google Scholar 

  54. Pu S, Fan C, Miao W, Liu G (2008) New photochromic diarylethenes with a six-membered aryl unit. Tetrahedron 64:9464–9470

    Article  CAS  Google Scholar 

  55. Tsivgoulis GM, Lehn J-M (1996) Photoswitched and functionalized oligothiophenes: synthesis and photochemical and electrochemical properties. Chem Eur J 2:1399–1406. doi:10.1002/chem.19960021112

    Article  CAS  Google Scholar 

  56. Takami S, Irie M (2007) Photochromic properties of diarylethenes having 2, 4-diphenylphenylsubstituents in the amorphous and PMMA films. J Photochem Photobiol A: Chem 187:202–208. doi:10.1016/j.jphotochem.2006.10.024

    Article  CAS  Google Scholar 

  57. Andre’asson J, Straight SD, Moore TA, Moore AL, Gust D (2008) Molecular all-photonic encoder-decoder. J Am Chem Soc 130:11122–11128. doi:10.1021/ja802845z

    Article  Google Scholar 

  58. Andre’asson J, Pischel U, Straight SD, Moore TA, Moore AL, Gust D (2011) All-photonic multifunctional molecular logic device. J Am Chem Soc 133:11641–11648. doi:org/10.1021/ja203456h

    Article  Google Scholar 

  59. Straight SD, Liddell PA, Moore TA, Terazono Y, Moore AL, Gust D (2007) All-photonic molecular XOR and NOR logic gates based on photochemical control of fluorescence in a fulgimide–porphyrin–dithienylethene triad. Adv Funct Mater 17:777–785. doi:10.1002/adfm.200600802

    Article  CAS  Google Scholar 

  60. Areephong J, Hurenkamp JH, Milder MTW, Meetsma A, Herek JL, Browne WR, Feringa BL (2009) Photoswitchable sexithiophene-based molecular wires. Org Lett 11:721–724. doi:10.1021/ol8028059

    Article  CAS  Google Scholar 

  61. Yin J, Lin Y, Cao X, Yu G-A, Liu SH (2008) Novel photochromic macrocycles composed of thiophene and ethylene building blocks: synthesis, structure, and photochromic property. Tetrahedron Lett 49:1582–1585

    Article  CAS  Google Scholar 

  62. Jung I, Choi H, Kim E, Lee C-H, Kang SO, Ko J (2005) Synthesis and photochromic reactivity of macromolecules incorporating four dithienylethene units. Tetrahedron 61:12256–12263. doi:10.1016/j.tet.2005.09.099

    Article  CAS  Google Scholar 

  63. Krayushkin MM, Kalik MA, Dzhavadov DL, Vorontsova LG, Starikova ZA, Martynkin AYu, Ivanov VL, Uzhinov BM (2000) Photochromic dihеtarylethenes 5 synthesis, structure andphotochromic properties of 4,4′-disubstituted 1,2-bis[2-ethyl-5-ethylthio(etrhylsulfonyl)-3-thienyl]perfluorcyclopentenes. Izv Acad Nauk Ser Khim 1778–1784

    Google Scholar 

  64. Hanazawa M, Sumiya R, Horikawa Y, Irie M (1992) Thermally irreversible photochromic systems. Reversible photocyclization of 1, 2-bis (2-methylbenzo[b]thiophen-3-yl)perfluorocyclocoalkene derivatives. J Chem Soc Chem Commun 206–207. doi:10.1039/C39920000206

  65. Irie M, Uchida K (1998) Synthesis and properties of photochromic diarylethenes with heterocyclic aryl groups. Bull Chem Soc Jpn 71:985–996

    Article  CAS  Google Scholar 

  66. Yarovenko VN, Es’kov AA, Semenov SL, Zavarzin IV, Kadentsev VI, Kalik MA, Krayushkin MM, Strokach YP, Valova TM, Golotiuk ZO, Barachevsky VA (2005) Photochromic 1,2-dihetarylethenes with perfluorocyclopentene bridge: synthesis and spectral and kinetic study. Russ Chem Bull Int Ed 54:2790–2794

    Article  CAS  Google Scholar 

  67. Morimitsu K, Kobatake S, Irie M (2004) Large geometrical structure changes of photochromic diarylethenes upon photoirradiation. Tetrahedron Lett 45:1155–1158. doi:10.1016/j.tetlet.2003.12.005

    Article  CAS  Google Scholar 

  68. Krayushkin MM, Migulin VA, Yarovenko VN, Barachevskii VA, Vorontsova LG, Starikova ZA, Zavarzin IV, Bulgakova VN (2007) Synthesis and characterisation of 1, 2-dihetarylethenes containing chlorobenzothiophene moieties. Mendeleev Commun 17:125–127. doi:10.1016/j.mencom.2007.03.025

    Article  CAS  Google Scholar 

  69. Uno K, Niikura H, Morimoto M, Ishibashi Y, Miyasaka H, Irie M (2011) In situ preparation of highly fluorescent dyes upon photoirradiation. J Am Chem Soc 133:13558–13564. doi:org/10.1021/ja204583e

    Article  CAS  Google Scholar 

  70. Jeong YC, Yang SI, Kim E, Ahn KH (2006) Development of highly fluorescent photochromic material with high fatigue resistance. Tetrahedron 62:5855–5861. doi:10.1016/j.tet.2006.04.029

    Article  CAS  Google Scholar 

  71. Jeong YC, Han JP, Kim Y, Kim E, Yang SI, Ahn KH (2007) Characterization and photophysical properties of sulfur-oxidized diarylethenes. Tetrahedron 63:3173–3182. doi:10.1016/j.tet.2007.02.007

    Article  CAS  Google Scholar 

  72. Yeo KM, Gao CJ, Ahn KH, Lee IS (2008) Superparamagnetic iron oxide nanoparticles with photoswitchable fluorescence. Chem Commun 4622–4624. doi:10.1039/B807462C

  73. Jeong YC, Park DG, Lee IS, Yang SI, Ahn KH (2009) Highly fluorescent photochromic diarylethene with an excellent fatigue property. J Mater Chem 19:97–103. doi:10.1039/b814040e

    Article  CAS  Google Scholar 

  74. Kim E, Kim M, Kim K (2006) Diarylethenes with intramolecular donor–acceptor structures for photoinduced electrochemical change. Tetrahedron 62:6814–6821. doi:10.1016/j.tet.2006.04.089

    Article  CAS  Google Scholar 

  75. Wang T, Liu G, Liu W, Cui S (2012) Synthesis of a novel photochromic diarylethene for polarization optical recording. Adv Mater Res 396–398: 2357–2360. doi:10.4028/www.scientific.net/AMR.396-398.2357

  76. (a) Krayushkin MM, Kalik МA, Kozhinov DV, Martynkin Au, Strokach YP, Barachevskii VA (2005) Synthesis and photochemical properties of 1, 2-bis{2-ethyl-5-(benzothiazol-2-yl)thieno[2,3-b]thiophene-3-yl}hexafluorocyclopentene. Khim Geterotsikl Soedin 360–364; (b) Krayushkin MM, Stoyanovich FM, Zolotarskaya OY, Murav’ev IV, Martynkin Ayu, Vorontsova LG, Starikova ZA, Ivanov VL, Uzhinov BM (2001) Russ Chem Bull Int Ed Engl 50:110–115

    Google Scholar 

  77. (a) Krayushkin MM, Stoyanovich FM, Zolotarskaya OYu, Yarovenko VN, Bulgakova VN, Zavarzin IV, Martynkin AYu (2002). Photochromic dihetarylethenes. 18. New approach to the synthesis of dithienothiophene and preparation of its photochromic derivative. Russ Chem Bull 51:2097–2099. doi:10.1023/A:1021676313508; (b) Wang H, Xu W, Zhu D (2012) Synthesis and photochromic reactivity of a new class of photochromic diarylethene dimer containing dithieno[3,2-b:2′3′-d]thiophene. Tetrahedron 68: 8719–8723. http://dx.doi.org/10.1016/j.tet.2012.08.026; (c) Wang H, Xu W, Zhu D (2013) Photochromism of diarylethenes containing dithieno[3,2-b:2′,3′-d]thiophene. Dyes Pigments 97:303–310. doi:10.1016/j.dyepig.2013.01.011

  78. Fujimoto Y, Ubukata T, Yokoyama Y (2008) Dendrimer diarylethenes: the memory effect of conformation in polymer matrices. Chem Commun 5755–5757. doi:10.1039/b812503a

  79. Iwato S, Ishihara Y, Qian CP, Tanaka K (1992) Thermal stability of photochromic bis[(trifluoromethyl)thiazolyl]ethene derivatives. J Org Chem 57:3726–3727. doi:10.1021/jo00039a040

    Article  Google Scholar 

  80. Uchida K, Ishikawa T, Takeshita M, Irie M (1998) Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-bis(thiazolyl)per-fluorocyclopentenes). Tetrahedron 54:6627–6638. doi:10.1016/S0040-4020(98)00330-5

    Article  CAS  Google Scholar 

  81. Giraud M, Le’austic A, Guillot R, Yu P, Lacroix PG, Nakatani K, Pansuc R, Maurel F (2007) Dithiazolylethene-based molecular switches for nonlinear optical properties and fluorescence: synthesis, crystal structure and ligating properties. J Mater Chem 17:4414–4425. doi:10.1039/B704806H

    Article  CAS  Google Scholar 

  82. Léaustic A, Anxolabéhère-Mallart E, Maurel F, Midelton S, Guillot R, Métivier R, Nakatani K, Yu P (2011) Photochromic and reductive electrochemical switching of a dithiazolylethene with large redox modulation. Chem Eur J 17:2246–2255. doi:10.1002/chem.201002451

    Article  Google Scholar 

  83. Giraud M, Leaustic A, Guillot R, Yu P, Maurel F, Nakatani K (2009) Easy and efficient tuning of the photochromic properties of 1,2-bis[5′-methyl-2′-(2″-pyridyl)thiazolyl]perfluorocyclopentene). Tetrahedron Lett 50:1485–1489. doi:10.1016/j.tetlet.2009.01.078

    Article  CAS  Google Scholar 

  84. Yamaguchi T, Irie M (2006) Photochromic and fluorescent properties of bisfurylethene derivatives. J Mater Chem 16:4690–4694. doi:10.1039/B611294C

    Article  CAS  Google Scholar 

  85. Yamaguchi T, Irie M (2005) Photochromism of bis(2-alkyl-1-benzofuran-3-yl)perfluorocyclopentene derivatives. J Org Chem 70:10323–10328. doi:10.1021/jo051372z

    Article  CAS  Google Scholar 

  86. Yamaguchi T, Irie M (2006) Photochromism of 1, 2-bis(2-alkyl-1-benzofuran-3-yl)perfluorocyclopentene derivatives. Eur J Org Chem 3105–3111. doi:10.1002/ejoc.200600011

  87. Yamaguchi T, Takami S, Irie M (2008) Photochromic properties of 1,2-bis(6-substitute-2-methyl-1-benzofuran-3-yl)ethene derivatives. J Photochem Photobiol A: Chem 193:146–152. doi:10.1016/j.jphotochem.2007.06.019

    Article  CAS  Google Scholar 

  88. Yamaguchi T, Taniguchi W, Kagawa T, Kamihashi Y, Ozeki T, Morimoto M, Irie M (2011) Photochromism of 1, 2-bis(5-n-alkyl-2-phenyloxazol-4-yl)perfluorocyclopentene derivatives in single-crystalline phase. Chem Lett 40:635–637. doi:10.1246/cl.2011.635

    Article  CAS  Google Scholar 

  89. Uchida K, Matsuoka T, Sayo K, Iwamoto M, Hayashi S, Irie M (1999) Thermally reversible photochromic systems. Photochromism of a dipyrrolylperfluorocyclopentene. Chem Lett 28:835–836

    Article  Google Scholar 

  90. Heynderickx A, Kaou AM, Moustrou C, Samat A, Guglielmetti R (2003) Synthesis and photochromic behaviour of new dipyrrolylperfluorocyclopentenes. New J Chem 27:1425–1432. doi:10.1039/B302623J

    Article  CAS  Google Scholar 

  91. Walko M, Feringa BL (2005) Synthesis and properties of dipyridylcyclopentenes. Mol Cryst Liq Cryst 431:549–553. doi:10.1080/15421400590947379

    Article  CAS  Google Scholar 

  92. (a) Takami S, Irie M (2004) Synthesis and photochromic properties of novel yellow developing photochromic compounds. Tetrahedron 60:6155–6161. doi:10.1016/j.tet.2004.05.029; (b) Liu G, Pu S, Wang X (2010) Photochromism of new 3,5-position hybrid diarylethene derivatives bearing both thiophene and thiazole moieties. Tetrahedron 66:8862–8871. doi:10.1016/j.tet.2010.09.066

  93. Pu S, Liu G, Shen L, Xu J (2007) Efficient synthesis and properties of isomeric photochromic diarylethenes having a pyrrole unit. Org Lett 9:2139–2142. doi:10.1021/ol070622q

    Article  CAS  Google Scholar 

  94. Liu G, Pu S, Wang X, Liu W, Yang T (2011) Effects of substitution on the optoelectronic properties of photochromic diarylethenes bearing a pyrrole moiety. Dyes Pigments 90:71–81. doi:10.1016/j.dyepig.2010.11.001

    Article  CAS  Google Scholar 

  95. Liu G, Pu S, Wang X (2010) Synthesis and the effect of substituent position upon unsymmetrical isomeric diarylethenes earing a pyrrole unit. J Photochem Photobiol A: Chem 214:230–240. doi:10.1016/j.jphotochem.2010.07.001

    Article  CAS  Google Scholar 

  96. Nakashima T, Miyamura K, Sakai T, Kawai T (2009) Photo-, solvent-, and ion-controlled multichromism of imidazolium-substituted diarylethenes. Chem Eur J 15:1977–1984. doi:10.1002/chem.200801192

    Article  CAS  Google Scholar 

  97. Pu S, Yang T, Xu J, Chen B (2006) Syntheses and properties of new photochromic diarylethene derivatives having a pyrazole unit. Tetrahedron Lett 47:6473–6477. doi:10.1016/j.tetlet.2006.06.073

    Article  CAS  Google Scholar 

  98. Tong Z, Pu S, Cui S (2012) Synthesis and properties of a new photochromic compound bearing isoxazol moiety. Adv Mater Res 399–401: 1119–1122. doi:10.4028/www.scientific.net/AMR.399-401.111910.4028/www.scientific.net/AMR.399-401.1119

  99. Pu S, Wang R, Liu G, Liu W, Cui S, Yan P (2012) Photochromism of new unsymmetrical diarylethene derivatives bearing both benzofuran and thiophene moieties. Dyes Pigments 94:195–206. doi:10.1016/j.dyepig.2012.01.003

    Article  CAS  Google Scholar 

  100. Pu S, Yan P, Liu G, Liu W, Miao W (2011) New photochromic diarylethenes bearing a pyridine moiety. Tetrahedron Lett 52:143–147. doi:10.1016/j.tetlet.2010.11.011

    Article  CAS  Google Scholar 

  101. Wang R, Pu S, Liu G, Cui S, Liu W (2012) New photochromic 1, 2-diarylperfluorocyclopentenes bearing unsymmetrical six-membered aryl units. Tetrahedron Lett 53:320–324. doi:10.1016/j.tetlet.2011.11.035

    Article  CAS  Google Scholar 

  102. Takami S, Irie M (2005) Photochemically stable novel yellow developing photochromic compounds having a thiazole group. Mol Cryst Liq Cryst 431:467–471. doi:10.1080/15421400590947144

    Article  CAS  Google Scholar 

  103. Pu S, Li H, Liu G, Liu W (2010) Photochromism of new diarylethenes bearing both thiazole and benzene moieties. Tetrahedron Lett 51:3575–3579. doi:10.1016/j.tetlet.2010.05.004

    Article  CAS  Google Scholar 

  104. Yamaguchi T, Irie M (2006) Photochromism of diarylethene derivatives having an indene unit. Tetrahedron Lett 47:1267–1269. doi:10.1016/j.tetlet.2005.12.074

    Article  CAS  Google Scholar 

  105. Liu W, Wang W, Fan C, Liu G (2012) Synthesis and properties of a photochromic switch Adv Mater Res 396–398: 2431–2433. doi:10.4028/www.scientific.net/AMR.396-398.2431

  106. Yamaguchi T, Irie M (2006) Photochromism of diarylethene derivatives having n-alkylbenzothiophene and n-alkylbenzofuran units. Bull Chem Soc Jpn 79:1100–1105. doi:10.1246/bcsj.79.1100

    Article  CAS  Google Scholar 

  107. Yamaguchi T, Uchida K, Irie M (2008) Properties of diarylethene derivatives having benzofuran and benzothiophene rings based on regioisomers. Bull Chem Soc Jpn 81:644–652. doi:10.1246/bcsj.81.644

    Article  CAS  Google Scholar 

  108. Yamaguchi T, Hosaka M, Ozeki T, Morimoto M, Irie M (2011) Photochromism of diarylethene derivatives bearing a benzo[b]silole unit. Tetrahedron Lett 52:5601–5604. doi:10.1016/j.tetlet.2011.08.063

    Article  CAS  Google Scholar 

  109. Ushiogi Y, Hase T, Iinuma Y, Takata A, Yoshida J (2007) Synthesis of photochromic diarylethenes using a microflow system. Chem Commun 43:2947–2949. doi:10.1039/b702277h

    Article  Google Scholar 

  110. Asai T, Takata A, Nagaki A, Yoshida J (2012) Practical synthesis of photochromic diarylethenes in integrated flow microreactor systems. ChemSusChem 5:339–350. doi:10.1002/cssc.201100376

    Article  CAS  Google Scholar 

  111. Hiroto S, Suzuki K, Kamiya H, Shinokubo H (2011) Synthetic protocol for diarylethenes through Suzuki–Miyaura coupling. Chem Commun 47:7149–7151. doi:10.1039/c1cc12020d

    Article  CAS  Google Scholar 

  112. Beydoun K, Roger J, Boixel J, Le Bozec H, Guerchais V, Doucet H (2012) A straightforward access to photochromic diarylethene derivatives via palladium-catalysed direct heteroarylation of 1,2-dichloroperfluorocyclopentene. Chem Commun 48:11951–11953 [117] (112). doi:10.1039/C2CC37046H

  113. Chambers RD, Edwards AR (1997) Perfluorocarbon fluids as solvent replacements. J Chem Soc Perkin Trans 1:3623–3628. doi:10.1039/A704823H

    Article  Google Scholar 

  114. Lucas LN, van Esch JH, Kellogg RM, Feringa BL (1999) A new synthetic route to symmetrical photochromic diarylperfluorocyclopenthenes. Tetrahedron Lett 40:1775–1778. doi:10.1016/S0040-4039(98)02688-4

    Article  CAS  Google Scholar 

  115. Lucas LN, de Jong JJD, van Esch JH, Kellog RM, Feringa BL (2003) Syntheses of dithienylcyclopentene optical molecular switches. Eur J Org Chem 155–166. doi:10.100 2/1099-0690(200301)2003:1<155

  116. Hermes S, Dassa G, Toso G, Bianco A, Bertarelli C, Zerbi G (2009) New fast synthesis route for symmetric and asymmetric phenyl substituted photochromic dithienylethenes bearing functional groups such as alcohols, carboxylic acids, or amines. Tetrahedron Lett 50:1614–1617. doi:10.1016/j.tetlet.2009.01.102

    Article  CAS  Google Scholar 

  117. Krayushkin MM, Kalik MA, Migulin VA (2009) McMurry reaction in the synthesis of photochromic dihetarylethenes. Russ Chem Rev 78:329–336. doi:10.1070/RC2009v078n04ABEH004018

    Article  CAS  Google Scholar 

  118. Kobatake S, Imao S, Yamashiro Y, Terakawa Y (2011) Photoswitching of an alcohol-sensitive photochromic diarylethene. Tetrahedron Lett 52:1905–1908. doi:10.1016/j.tetlet.2011.02.039

    Article  CAS  Google Scholar 

  119. Kobatake S, Irie M (2004) Single-crystalline photochromism of diarylethenes. Bull Chem Soc Jpn 77:195–210

    Article  CAS  Google Scholar 

  120. Morimoto M, Kobatake S, Irie M (2004) Crystal engineering of photochromic diarylethene single crystals. Chem Rec 4:23–38

    Article  CAS  Google Scholar 

  121. Kuroki L, Takami S, Yoza K, Morimoto M, Irie M (2010) Photoinduced shape changes of diarylethene single crystals: correlation between shape changes and molecular packing. Photochem Photobiol Sci 9:221–225

    Article  CAS  Google Scholar 

  122. Kobatake S, Hasegawa H, Miyamura K (2011) High-convertible photochromism of a diarylethene single crystal accompanying the crystal shape deformation. Cryst Growth Des 11:1223–1229. dx.doi.org/10.1021/cg101448m

  123. Kobatake S, Yamada T, Uchida K, Kato N, Irie M (1999) Photochromism of 1,2-Bis(2,5-dimethyl-3-thienyl)perfluorocyclopentene in a single crystalline phase. J Am Chem Soc 121:2380–2386

    Article  CAS  Google Scholar 

  124. Yamada T, Kobatake S, Irie M (2000) X-Ray crystallographic study on single-crystalline photochromism of 1,2-Bis(2,5-dimethyl-3-thienyl) perfluorocyclopentene. Bull Chem Soc Jpn 73:2179–2184

    Article  CAS  Google Scholar 

  125. Vorontsova LG, Krayushkin MM, Starikova ZA, Kalik MA, Stoyanovich FM, Zolotarskaya OYu, Dzhavadov DL (2000) Molecular and crystal structure of 1, 2-bis(2-ethyl-5-ethylsulfonylthien-3-yl) perfluorocyclopentene and 1,2-bis[5-(benzoxazol-2-yl)-2-methylthien-3-yl]perfluorocyclopentene. Izv Akad Nauk Ser Khim 74–76

    Google Scholar 

  126. Kobatake S, Uchida K, Tsuchida E, Irie M (2002). Single-crystalline photochromism of diarylethenes: reactivity–structure relationship. Chem Commun 2804–2805. doi:10.1039/b208419h

  127. Liu G, Liu M, Pu S, Fan C, Cui S (2012) Photochromism of new unsymmetrical isomeric diarylethenes bearing a pyridine group. Tetrahedron 68:2267–2275

    Article  CAS  Google Scholar 

  128. Morimoto M, Irie M (2005) Photochromism of diarylethene single crystals: crystal structures and photochromic performance. Chem Commun 3895–3905. doi:10.1039/B505256D

  129. (a) Ramamurthy V, Venkatesan K (1987) Photochemical reactions of organic crystals. Chem Rev 87 433–481 doi:10.1021/cr00078a009; (b) Morimoto M, Irie M (2006) Photochromic reactions of diarylethenes in single crystals with intermolecular OH···N hydrogen-Bonding networks. Chem Eur J 12:4275–4282

  130. Krayushkin MM, Vorontsova LG, Uzhinov BM (2001) The structure and characteristics of photochromic dithienylethenes. Int J Photoenergy 3:25–32

    Article  CAS  Google Scholar 

  131. Kobatake S, Yamada M, Yamada T, Irie M (1999) Photochromism of 1,2-bis(2-methyl-6-nitro-1-benzothiophen-3-yl)-perfluorocyclopentene in a single-crystalline phase: dichroism of the closed-ring form isomer. J Am Chem Soc 121:8450–8456. doi:10.1021/ja991013

    Article  CAS  Google Scholar 

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Acknowledgement

The authors are grateful to Dr. Ludmila Vorontsova who has partly contributed in the work described herein.

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  1. Laboratory of Heterocyclic Compounds, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Leninsky prospect 47, Russia

    M. M. Krayushkin & M. A. Kalik

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  1. M. M. Krayushkin
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Correspondence to M. M. Krayushkin .

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  1. Department of Chemistry, Moscow State University, Moscow, Russia

    Valentine Nenajdenko

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Krayushkin, M.M., Kalik, M.A. (2014). 1,2-Bis(Hetaryl)Perfluorocyclopentenes as Unique Thermally Irreversible Photochromes. Synthesis and Structural Singularities. In: Nenajdenko, V. (eds) Fluorine in Heterocyclic Chemistry Volume 1. Springer, Cham. https://doi.org/10.1007/978-3-319-04346-3_12

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