Skip to main content

Fulgide Family Compounds: Synthesis, Photochromism, and Applications

  • Chapter
Book cover Organic Photochromic and Thermochromic Compounds

Part of the book series: Topics in Applied Chemistry ((TAPP))

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. J. Whittall, 4n + 2 Systems: fulgides, in: Photochromism: Molecules and Systems (H. Durr and H. Bouas-Laurent, eds.), pp. 467–492, Elsevier, Amsterdam (1990).

    Google Scholar 

  2. J. Whittall, Fulgides and fulgimides—a promising class of photochromes for application, in: Applied Photochromic Polymer System (C. B. McArdle, ed.), pp. 80–120, New York (1991).

    Google Scholar 

  3. H. G. Heller, C. C. Elliot, K. Koh, S. Al-Shihry, and J. Whittall, The design and development of photochromic systems for commercial applications, Spec. Publ.-R. Soc. Chem., 125, 156–168 (1993).

    CAS  Google Scholar 

  4. H. Stobbe, A product of the action of light on diphenylfulgide and the polymerization of phenylpropiolic acid, Berichte, 40, 3372–3382 (1907).

    CAS  Google Scholar 

  5. W. S. Johnson and G. H. Daub, The Stobbe condensation, Organic Reactions, 6, Chap. 1, pp. 1–73, John Wiley & Sons, Inc., New York (1951).

    Google Scholar 

  6. H. G. Heller and M. Szewczyk, Overcrowded molecules. Part X. Photoreactions of photochromic (α-phenylethylidene) (substituted methylene) succinic anhydrides, J. Chem. Soc., Perkin. Trans. 1, 1974, 1487–1492.

    Google Scholar 

  7. Y. Yokoyama, T. Serizawa, S. Suzuki, Y. Yokoyama, and Y. Kurita, Fulgenolides thermally irreversible photochromic lactones with large quantum yields of photoreactions, Chem. Lett., 1995, 17–18.

    Google Scholar 

  8. Y. Yokoyama, K. Sugiyama, S. Yamada, H. Takimoto, and Y. Kurita, Fulgenates. A new class of fulgide-related irreversible photochromic system, Chem. Lett., 1994, 749–752.

    Google Scholar 

  9. A. Santiago and R. S. Becker, Photochromic fulgides. Spectroscopy and mechanism of photoreactions, J. Am. Chem. Soc., 90, 3654–3658 (1968).

    Article  CAS  Google Scholar 

  10. C. Lenoble and R. S. Becker, Photophysics, photochemistry, and kinetics of photochromic fulgides. J. Phys. Chem., 90, 2651–2654 (1986).

    CAS  Google Scholar 

  11. D. A. Parthenopoulos and P. M. Rentzepis, Transient spectroscopy of a photochromic fulgide, J. Mol. Struc., 224, 297–302 (1990).

    Article  CAS  Google Scholar 

  12. S. Kurita, A. Kashiwagi, Y. Kurita, H. Miyasaka, and N. Mataga, Picosecond laser photolysis studies on the photochromism of a furyl fulgide, Chem. Phys. Lett., 171, 553–557 (1990).

    Article  CAS  Google Scholar 

  13. J. Takeda, T. Tayu, S. Kurita, Y. Yokoyama, Y. Kurita, T. Kuga, and M. Matsuoka, Radiative and non-radiative decay processes of the excited state of the colored form of photochromic furyl fulgide, Chem. Phys. Lett., 220, 443–447 (1994).

    Article  CAS  Google Scholar 

  14. W. Zhao, Y. Ming, Z. Zhu, and M. Fan, Mechanism of photochromic reaction of (E)-α-(1,2,4,5-tetamethyl-3-pyrryl) ethylidene (isopropylidene) succinic anhydride, J. Photochem. Photobiol. A: Chem., 63, 235–240 (1992).

    Article  CAS  Google Scholar 

  15. L. Yu, Y. Ming, and M. Fan, Studies on the photochromic mechanism of 1,2,-dimethyl-5-phenyl-3-pyrryl succinic anhydride, Res. Chem. Intermed., 13, 829–838 (1993).

    Google Scholar 

  16. H. G. Heller and M. Szewczyk, Synthesis, stereochemistry, and isomerisation of phenylethylidene succinic esters and related compounds, J. Chem. Soc., Perkin. Trans. 1, 1974, 1483–1487.

    Google Scholar 

  17. R. J. Hart, H. G. Heller, R. M. Megit, and M. Szewczyk, Overcrowded molecules. Part XIII. Thermally stable photochromic systems involving (E)-2-isopropylidene-3-(naphthylmethylene) succinic anhydrides and N-phenylimides, J. Chem. Soc., Perkin. Trans. 1, 1975, 2227–2232.

    Google Scholar 

  18. H. G. Heller and R. M. Megit, Overcrowded molecules. Part IX. Fatigue-free photochromic systems involving (E)-2-isopropylidene-3-(mesitylmethylene)-succinic anhydride and N-phenylimide, J. Chem. Soc., Perkin. Trans. 1, 1974, 923–927.

    Google Scholar 

  19. P. J. Darcy, R. J. Hart, and H. G. Heller, Overcrowded molecules. Part 14. Photochromic systems involving (Z)-1-methylpropylidene (diphenylmethylene)-succinic and (E)-3,5-dimethoxybenzyli-dene (alkyl-substituted methylene) succinic anhydrides, J. Chem. Soc., Perkin. Trans. 1, 1978, 571–576.

    Google Scholar 

  20. H. G. Heller, S. Oliver, and M. Shawe, Overcrowded molecules. Part 17. Thermal reactions of (α-phenylethylidene) (substituted methylene) succinic anhydrides, J. Chem. Soc., Perkin. Trans. 1, 1979, 154–157.

    Google Scholar 

  21. P. J. Darcy, H. G. Heller, S. Patharakorn, R. D. Piggott, and J. Whittall, Photochromic systems. Part 1. Photochemical studies on (E)-2-isopropylidene-3-[1-(3,4,5-trimethoxyphenyl) ethylidene] succinic anhydride and related compounds, J. Chem. Soc., Perkin. Trans. 1, 1986, 315–319.

    Google Scholar 

  22. P. A. Davidse, J. L. M. Dillen, A. M. Heyns, T. A. Modro, and P. H. van Rooyen, Photochromic systems. Part 1. Structural and spectroscopic study of photochemically active products of Stobbe condensation. 2,3-dibenzylidene-succinic acid and its anhydride, Can. J. Chem., 68, 741–746 (1990).

    CAS  Google Scholar 

  23. J. C. A. Boeyens, L. Denner, and G. W. Perold, Rotamers and isomers in the fulgide series. Part 2. Stereochemistry and conformational analysis of bis-(p-methoxybenzylidene) succinic anhydrides by X-ray crystallography and molecular mechanics, J. Chem. Soc., Perkin. Trans. 2, 1988, 1999–2005.

    Google Scholar 

  24. R. J. Hart and H. G. Heller, Overcrowded molecules. Part VII. Thermal and photochemical reactions of photochromic (E)-and (Z)-benzylidene (diphenylmethylene) succinic anhydrides and imides, J. Chem. Soc., Perkin. Trans. 1, 1972, 1321–1324.

    Google Scholar 

  25. H. D. Ilge and H. Schutz, Photochemistry of fulgides. 18, 1H-nuclear resonance of phenyl fulgides, J. Prakt., Chem., 326,863–875 (1984).

    CAS  Google Scholar 

  26. H. D. Ilge, R. Paetzold, and R. Radeglia, Photochemistry of fulgides. XI, Carbon-13 nuclear resonance spectra of phenyl fulgides, J. Prakt. Chem., 326, 222–232 (1984).

    CAS  Google Scholar 

  27. M. D. Cohen, H. W. Kaufman, D. Sinnreich, and G. M. J. Schmidt, Photoreactions of di-p-anisylidene fulgide (di-p-anisylidene succinic anhydride), J. Chem. Soc. (B), 1970, 1035–1039.

    Google Scholar 

  28. J. C. A. Boeyens, L. Denner, and G. W. Perold, Rotamers and isomers in the fulgide series. Part 1. Stereochemistry and conformational analysis of bis-(3,4-dimethoxybenzylidene) succinic anhydrides by X-ray crystallography and molecular mechanics, J. Chem. Soc., Perkin. Trans. 2, 1988, 1749–1758.

    Google Scholar 

  29. J. C. A. Boeyens, C. C. Allen, and G. W. Perold, Rotamers and isomers in the fulgide series. Part 3. Structures of the bis-(4-methoxy-3-methylbenzylidene) succinic anhydrides, J. Chem. Soc., Perkin. Trans. 2, 1993, 1161–1165.

    Google Scholar 

  30. H. D. Ilge, C. Drawert, J. Suehnel, and R. Paetzold, Photochemistry of fulgides. XII. Electronic and steric substituent effects on the UV/visible absorption spectra of phenyl fulgide, J. Prakt. Chem., 326, 233–247 (1984).

    CAS  Google Scholar 

  31. H. D. Ilge, Photochemistry of phenyl fulgides. XX. Absence of activation barriers for photoisome-rization reactions in the excited singlet state of extremely sterically hindered α, δ-di-(4-alkoxyphenyl) fulgide isomers, J. Photochem., 33, 333–347 (1986).

    CAS  Google Scholar 

  32. A. Tomoda, A. Kaneko, H. Tsuboi, and R. Matsushima, Effect of two electron-donating substituents on photochromism of aryl fulgide, 2-(2,6-dimethyl-3,5-substituted benzylidene)-3-isopropylidene succinic anhydride, Bull. Chem. Soc. Jpn., 65, 2352–2358 (1992).

    CAS  Google Scholar 

  33. V. A. Kumar and K. Venkatesan, Studies on photochromism of a thermally stable fulgide in the crystalline state: X-ray crystallographic investigation of (E)-2-isopropylidene-3-(1-naphthyl methylene) succinic anhydride, Acta Cryst., B49, 896–900 (1993).

    CAS  Google Scholar 

  34. S. Goldschmidt, R. Riedle, and A. Reichardt, Bisbiphenylene fulgides and the cleavage of disbiphenylene fulgenic acid to optically active components, Ann., 604, 121–132 (1957).

    CAS  Google Scholar 

  35. H. G. Heller and M. Jottaway, Intramolecular [4 + 4] photocycloaddition reactions of the photochromic compounds, 3,4-bis(9-anthryl methylene)-tetrahydrofuran-2,5-dione and its 5-dicyanomethylene derivative, J. Chem. Soc., Chem. Commun., 1995, 479–480.

    Google Scholar 

  36. R. W. McCabe, D. E. Parry, and S. P. Saberi, Organometallic fulgides. Part 1. Synthesis and photochemistry of ferrocenyl fulgides [ferrocenyl ethylidene (isopropylidene) succinic anhydrides], J. Chem. Soc., Perkin. Trans. 1, 1993, 1023–1029.

    Google Scholar 

  37. P. J. Darcy, H. G. Heller, P. J. Strydom, and J. Whittall, Photochromic heterocyclic fulgides. Part 2. Electrocyclic reactions of (E)-α-2,5-dimethyl-3-furylethylidene (alkyl-substituted methylene) succinic anhydrides, J. Chem. Soc., Perkin. Trans. 1, 1981, 202.

    Google Scholar 

  38. H. G. Heller and J. R. Langan, Photochromic heterocyclic fulgides. Part 3. The use of (E)-α-(2,5-dimethyl-3-furylethylidene) (isopropylidene) succinic anhydride as a simple convenient chemical actinometer, J. Chem. Soc., Perkin. Trans. 2, 1981, 341.

    Google Scholar 

  39. H. G. Heller, The development of photochromic compounds for use in optical information storage, Chem. Ind., 1978, 193–196.

    Google Scholar 

  40. H. G. Heller, Organic fatigue-resistant photochromic imaging materials, IEE Proc., 130(1), 209–211 (1983).

    CAS  Google Scholar 

  41. A. P. Glaze, S. A. Harris, H. G. Heller, W. Johncock, S. N. Oliver, P. J. Strydom, and J. Whittall, Photochromic heterocyclic fulgides. Part 4. The thermal and photochemical reactions of (E)isopro-pylidene [α-2-and-(3-thienyl)ethylidene] succinic anhydrides and related compounds, J. Chem. Soc., Perkin. Trans. 1, 1985, 957–961.

    Google Scholar 

  42. Y. Yokoyama, T. Goto, T. Inoue, M. Yokoyama, and Y. Kurita, Fulgides as efficient photochromic compounds role of the substituent on furyl alkylidene moiety of furyl fulgides in the photoreaction, Chem. Lett., 1988, 1049–1052.

    Google Scholar 

  43. Y. Yokoyama, T. Iwai, N. Kera, I. Hitomi, and Y. Kurita, Steric effect of alkylidene groups of furyl fulgides on the photochromic behavior, Chem. Lett., 1990, 263–264.

    Google Scholar 

  44. Y. Yokoyama, T. Inoue, M. Yokoyama, T. Goto, T. Iwai, N. Kera, I. Hitomi, and Y. Kurita, Effects of bulkiness of substituents on quantum yields of photochromic reactions of furyl fulgides, Bull. Chem. Soc. Jpn., 67, 3297–3303 (1994).

    CAS  Google Scholar 

  45. J. Kiji, T. Okano, H. Kitamura, Y. Yokoyama, S. Kubota, and Y. Kurita, Synthesis and photochromic properties of fulgides with a t-butyl substituent on the furyl or thienyl methylidene moiety, Bull. Chem. Soc. Jpn., 68, 616–619 (1995).

    CAS  Google Scholar 

  46. J. Hibino and E. Ando, Photochromic fulgide derivatives, Jpn. Kokai Tokyo Koho JP, 62,242,677 (Chem. Abstr. 109, 14838k).

    Google Scholar 

  47. H. G. Heller, New fatigue-resistant organic photochromic materials, in: Fine Chemicals for the Electronics Industry (P. Bamfield, ed.), pp. 120–135, Royal Soc. Chem., London (1986).

    Google Scholar 

  48. A. P. Glaze, H. G. Heller, and J. Whittall, Photochromic heterocyclic fulgides. Part 7. (E)-Adamantylidene-[1-(2,5,-dimethyl-3-furyl)ethylidene] succinic anhydride and derivatives: Model photochromic compounds for optical recording materials, J. Chem. Soc., Perkin. Trans. 2, 1992, 591–594.

    Google Scholar 

  49. A. Tomoda, A. Kaneko, H. Tsuboi, and R. Matsushima, Photochromism of heterocyclic fulgides. IV. Relationship between chemical structure and photochromic performance, Bull. Chem. Soc. Jpn., 66, 330–333 (1993).

    CAS  Google Scholar 

  50. H. G. Heller, Novel photoactive compounds, WO 91/01312, PCT/GB 90/01118 (1991).

    Google Scholar 

  51. V. Deblauwe and G. Smets, Quantum yields of the photochromic reactions of heterocyclic fulgides and fulgimides, Makromol. Chem., 189, 2503–2512 (1988).

    Article  CAS  Google Scholar 

  52. K. Horie, K. Hirao, N. Kenmochi, and I. Mita, Photochromic reactions of spirobenzopyran, azo-benzene and fulgide at 4 K in polymer films, Makromol. Chem. Rapid Commun., 9, 267–273 (1988).

    Article  CAS  Google Scholar 

  53. Y. Yokoyama, H. A. Hayata, H. Ito, and Y. Kurita, Photochromism of a furyl fulgides, 2-[1-(2,5-dimethyl-3-furyl)ethylidene]-3-isopropylidene succinic anhydride in solvents and polymer films, Bull. Chem. Soc. Jpn., 63, 1607–1610 (1990).

    CAS  Google Scholar 

  54. S. Murakami, T. Tsutsui, R. Tanaka, and S. Saito, Quantum yield determination of photochemical reaction of photochromic compounds in solid films, Nippon Kagaku Kaishi, 1985, 1598.

    Google Scholar 

  55. J. Takeda, N. Nakayama, N. Nagase, T. Tayu, K. Kainuma, S. Kurita, Y. Yokoyama, and Y. Kurita, Intermolecular interaction of photochromic furyl fulgides dispersed in a polymer film, Chem. Phys. Lett., 198, 609–614 (1992).

    CAS  Google Scholar 

  56. Y. Yoshioka, T. Tanaka, M. Sawada, and M. Irie, Molecular and crystal structures of E-and Z-isomers of 2,5-dimethyl-3-furyl ethylidene (isopropylidene)-succinic anhydride, Chem. Lett., 1989, 19–22.

    Google Scholar 

  57. Y. Yokoyama, T. Iwai, M. Yokoyama, and Y. Kurita, Helical chirality and enantiotopomerization process of a photochromic furyl fulgide, Chem. Lett., 1994, 225–226.

    Google Scholar 

  58. A. P. Glaze, S. A. Harris, H. G. Heller, W. Johncock, S. N. Oliver, P. J. Strydom, and J. Whittall, Photochromic heterocyclic fulgides. Part 4.1. The thermal and photochromic reactions of (E)-isopropylidene-[α-(2-and-(3-thienyl ethylidene] succinic anhydrides and related compounds, J. Chem. Soc., Perkin. Trans. 1, 1985, 958–961.

    Google Scholar 

  59. K. Ulrich, H. Port, and P. Bauerle, Photochromic thiophene fulgide absorption spectra and kinetics of photochemical isomerizations, Chem. Phys. Lett., 155, 437–442 (1989).

    Article  CAS  Google Scholar 

  60. K. Ulrich, H. Port, H. C. Wolf, J. Wonner, F. Effenberger, and H. D. Ilge, Photochromic thiophene fulgides photokinetics of two isopropylidene derivatives, Chem. Phys., 154, 311–322 (1991).

    Article  CAS  Google Scholar 

  61. H. Konishi, A. Iwasa, S. Kudo, T. Okano, and J. Kiji, Synthesis and properties of long alkyl chain-substituted thienyl fulgides, Chem. Express, 5(7), 481–484 (1990).

    CAS  Google Scholar 

  62. A. Tomoda, A. Kaneko, H. Tsuboi, and R. Matsushima, Photochromism of heterocyclic fulgides, Bull. Chem. Soc. Jpn., 65, 1262–1267 (1992).

    CAS  Google Scholar 

  63. F. Effenberger and J. Wonner, Darstellung und photochemie eines (anthryl vinyl) thiophen-fulgides, Chem. Ber., 125, 2583–2590 (1992).

    CAS  Google Scholar 

  64. K. Kaftory, Photochromic and thermochromic compounds. I. Structures of(E) and (Z) isomers of 2-isopropylidene-3-[1-(2-methyl-5-phenyl)-3-thienylethylidene] succinic anhydride and the photo-product 7,7a-dihydro-4,7,7,7a-tetramethyl-2-phenylbenzo[b]thiophene 5,6-dicarboxylic anhydride (P), Acta Cryst., C40, 1015–1019 (1984).

    CAS  Google Scholar 

  65. V. I. Minkin, E. A. Medyantseva, T. Lyashik, A. V. Metelitsa, I. M. Andreeva, M. I. Knyazhankii, and N. V. Volbushiko, Photochromic fulgides of indole series, Khim. Geterosikl Soedin, 11, 1569–1570 (1986). (Chem. Abstr. 107, 58780, 1987).

    Google Scholar 

  66. H. Z. Wang, Synthesis and photochromic reactions of indolyl fulgides, Doctoral dissertation, Beijing Institute of Technology, Beijing, China (1989).

    Google Scholar 

  67. Y. Z. Li, Synthesis and photochromic properties of heterocyclic fulgides, Doctoral dissertation, Beijing Institute of Technology, Beijing, China (1990).

    Google Scholar 

  68. R. Matsushima, A. Kaneko, A. Tomoda, M. Ishizuka, and H. Suzuki, Photochemical fatigue resistances and thermal stabilities of heterocyclic fulgides in PMMA film, Bull. Chem. Soc. Jpn., 61(10), 3569–3573 (1988).

    Google Scholar 

  69. Y. Yokoyama and Y. Kurita, Synthesis and photoreactions of photochromic fulgides, J. Syn. Org. Chem. Jpn., 49(5), 364–372 (1991).

    CAS  Google Scholar 

  70. F. Wang, H. Z. Wang, Y. Z. Li, G. Y. Fan, X. S. Cui, and Z. C. Liu, Synthesis and crystal structure of azafulgides, Acta. Chimica. Sinica Engl. Ed., 4, 349–355 (1989).

    Google Scholar 

  71. G. Y. Fan, H. Z. Wang, X. S. Cui, Y. Z. Li, and H. S. Zhu, Crystal structures of 1,2-dimethyl-3-indolyl-methylidene succinic anhydride and 1,2-dimethyl-3-indolylethylidene succinic anhydride, Acta Physico-Chimica Sinica, 8(4), 545–549 (1992).

    CAS  Google Scholar 

  72. Y. Yokoyama and Y. Kurita, Photochromic properties of fulgides, Dyestuffs Chemicals, 37(6), 143–154 (1992).

    CAS  Google Scholar 

  73. Y. Yokoyama and Y. Kurita, Photochromic fulgides applicable to optical information storage, discovery of new nondestructive readout method, J. Chem. Soc. Jpn., Chem. Indus. Chem., 1992, 998–1006.

    Google Scholar 

  74. Y. Yokoyama, T. Tanaka, T. Yamane, and Y. Kurita, Synthesis and photochromic behavior of 5-substituted indolyl fulgides, Chem. Lett., 1991, 1125–1128.

    Google Scholar 

  75. S. Uchida, S. Yamada, Y. Yokoyama, and Y. Kurita, Steric effects of substituents on the photochromism of indolyl fulgide, Bull. Chem. Soc. Jpn., 68, 1677–1682 (1995).

    CAS  Google Scholar 

  76. H. G. Heller, Photochromic 3-pyrryl fulgides and fulgimides, EP, 0190016 (1986).

    Google Scholar 

  77. S. A. Harris, H. G. Heller, and S. N. Oliver, Photochromic heterocyclic fulgides. Part 5. Rearrangement reactions of (E)-α-1,2,5-trimethyl-3-pyrryl ethylidene (isopropylidene) succinic anhydride and related compounds, J. Chem. Soc., Perkin. Trans. 1, 1991, 3259–3262.

    Google Scholar 

  78. L. H. Yu, Y. F. Ming, W. L. Zhao, and M. G. Fan, Absorption spectra and photoisomerization kinetics of photochromic pyrryl fulgides, J. Photochem. Photobiol. A: Chem., 63, 235–240 (1992).

    Google Scholar 

  79. L. H. Yu, Y. F. Ming, and M. G. Fan, Synthesis, photochromic properties of pyrryl substituted heterocyclic fulgides, Chin. Chem. Lett., 4(3), 199–202 (1993).

    Google Scholar 

  80. W. L. Zhao, Z. L. Du, Z. Q. Zhu, L. H. Yu, Y. F. Ming, and M. G. Fan, Synthesis and photochromic behaviors of 1-long hydrocarbon chain-substituted pyrryl fulgides, Chin. Chem. Lett., 6, 573–576 (1995).

    CAS  Google Scholar 

  81. L. H. Yu, Y. F. Ming, W. L. Zhao, and M. G. Fan, Synthesis and solvent effect on absorption spectra of pyrryl-substituted fulgides, Youji Huaxue (Chin. J. Org. Chem.), 13, 590–596 (1993).

    Google Scholar 

  82. L. H. Yu, Y. F. Ming, W. L. Zhao, and M. G. Fan, Studies on photochromic mechanism and applications of pyrryl-substituted fulgides, Mol. Crys. Liq. Cryst., 246, 49–58 (1994).

    CAS  Google Scholar 

  83. L. H. Yu, Y. F. Ming, X. Y. Zhang, M. G. Fan, N. Y. Lin, and S. D. Yao, Nanosecond laser photolysis studies of photochromic processes in pyrryl fulgides, J. Photochem. Photobiol. A: Chem., 74, 37–41 (1993).

    Article  CAS  Google Scholar 

  84. L. H. Yu, Y. F. Ming, and M. G. Fan, Photochromic reactions of pyrryl-substituted fulgides and fulgimides, Science in China (B), 39(2), 179–184 (1996).

    CAS  Google Scholar 

  85. M. G. Fan, Y. F. Ming, L. H. Yu, X. Y. Zhang, X. J. Meng, Y. C. Liang, and Z. Yang, Photochromic fulgides and spirooxazines: mechanism and substituent effect on photoreactions, Science in China (B), 39(2), 144–149 (1996).

    CAS  Google Scholar 

  86. L. H. Yu, Y. F. Ming, and M. G. Fan, Studies on photoinduced electron transfer reaction between pyrryl-substituted fulgide and tetracyanoquinodimethane, Chin. Sci. Bull., 38(21), 1775–1778 (1993).

    CAS  Google Scholar 

  87. L. H. Yu, Y. F. Ming, M. G. Fan, and Y. Zhu, Synthesis and X-ray structures of a new pyrryl-substituted photochromic fulgide, Chin. Chem. Lett., 6(4), 297–300 (1995).

    CAS  Google Scholar 

  88. C. Reichardt, Solvatochromic dyes as solvent polarity indicators, Chem. Rev., 94, 2319–2358 (1994).

    Article  CAS  Google Scholar 

  89. N. J. Turro, Modern Molecular Photochemistry, Chap. 5, Cummings, New York (1978).

    Google Scholar 

  90. H. Suzuki, A. Tomoda, M. Ishizuka, A. Kaneko, M. Furui, and R. Matsushima, Photochromism of 4-oxazolyl fulgides, Bull. Chem. Soc. Jpn., 62, 3968–3971 (1989).

    CAS  Google Scholar 

  91. J. Walz, K. Ulrich, H. Port, H. C. Wolf, J. Wonner, and F. Effenberg, Fulgides as switches for intramolecular energy transfer, Chem. Phys. Lett., 213, 321–324 (1993).

    Article  CAS  Google Scholar 

  92. I. Cabrera, A. Dittrich, and H. Ringsdorf, Thermally irreversible photochromic liquid crystal polymers, Angew. Chem. Int. Ed. Engl., 30, 76–78 (1991).

    Article  Google Scholar 

  93. S. Rubin and I. Willner, Photoregulation of the activities of proteins, Mol. Cryst. Liq. Cryst., 246, 201–205 (1994).

    CAS  Google Scholar 

  94. I. Willner, S. Rubin, J. Wonner, F. Effenberger, and P. Bauerle, Photoswitchable binding of substrates to proteins: photoregulated binding of α-D-mannopyranose to concanavalin A modified by a thiophenefulgide dye, J. Am. Chem. Soc., 114, 3150–3151 (1992).

    CAS  Google Scholar 

  95. I. Willner, M. Lion-Dagan, S. Rubin, J. Wonner, F. Effenberger, and P. Bauerle, Photoregulation of α-chymotrypsin activity in organic media: effects of bioimprinting, Photochem. Photobiol., 59, 491–496 (1994).

    CAS  Google Scholar 

  96. Y. Yokoyama, M. Miyasaka, S. Uchida, and M. Yokoyama, Cyclic fulgenates. Enlargement of quantum yield of coloring reaction of photochromic fulgenates, Chem. Lett., 1995, 479–480.

    Google Scholar 

  97. H. G. Heller, D. S. Hughes, M. B. Hursthouse, and K. V. S. Koh, A new class of photochromic compounds exemplified by E-5-dicyanomethylene-4-(dialkyl and dicycloalkyl)methylene[1-(2,5-methyl-3-furyl) and (2-methyl-5-phenyl-3-thienyl)ethylidene]tetrahydrofuran-2-ones, J. Chem. Soc., Chem. Commun., 1994, 2713–2714.

    Google Scholar 

  98. Z. Sun and R. S. Hosmane, Fulgides and photochromism. Synthesis of (E)-and (Z)-5-dicyano-methylene-4-dicyclopropylmethylene-3-[1-(2,5-dimethyl-3-furyl)ethylidene] tetrahydro-furan-2-one, Tetrahedron Lett., 36, 3453–3456 (1995).

    CAS  Google Scholar 

  99. L. H. Yu, Studies on synthesis, photochromic mechanism and applications of fulgides, Doctoral dissertation, Institute of Photographic Chemistry, Chinese Academy of Sciences, Beijing (1994).

    Google Scholar 

  100. L. H. Yu, D. B. Zhu, and M. G. Fan, Synthesis and photochromism of 5-dicyanomethylene-4-isopropylidene-3-[1-(1-p-methoxyphenyl-2-methyl-5-phenyl-3-pyrryl)-ethylidene] tetrahydrofuran-2-one, Mol. Cryst. Liq. Cryst., 297, 107–114 (1997).

    CAS  Google Scholar 

  101. K. Freudenberg and T. Kempermann, Fulgenic acids and their reduction products, Ann., 602, 184–199 (1957).

    CAS  Google Scholar 

  102. H.-D. Ilge and R. Paetzold, Direkte und sensibilisierte photoisomerisierung der α,δ-phenyl fulgide, J. Prakt. Chem., 326, 705–720 (1984).

    CAS  Google Scholar 

  103. H.-D. Ilge, M. Kaschke, and D. Khechinashvili, Photochemistry of phenyl fulgides. XXI: ultrafast photoisomerization and radiationless deactivation processes in α,δ-di-(4-alkoxyphenyl)-fulgides and α,δ-bifluorenyl fulgides, J. Photochem., 33, 349–358 (1986).

    CAS  Google Scholar 

  104. Y. Yokoyama and Y. Kurita, Photochromism of fulgides and related compounds, Mol. Cryst. Liq. Cryst., 246, 87–94 (1994).

    CAS  Google Scholar 

  105. H. G. Heller, S. N. Oliver, J. Whittall, W. Johncock, P. J. Darcy, and C. Trundle, Photochromic fused-ring organic compounds and their use in photoreactive lenses, U.K. Pat. Appl. G.B. 2146327A (1985).

    Google Scholar 

  106. L. H. Yu, Y. F. Ming, M. G. Fan, H. T. Yu, and Q. Q. Ye, Synthesis and applications of photochromic fulgides in information storage, Science in China (B), 39(1), 1–6 (1996).

    CAS  Google Scholar 

  107. F. Matsui, H. Taniguchi, Y. Yokoyama, K. Sugiyama, and Y. Kurita, Application of photochromic 5-dimethylaminoindolyl fulgide to photon-mode erasable optical memory media with non-destructive ability based on wavelength dependence of bleaching quantum yield, Chem. Lett., 1994, 1869–1872.

    Google Scholar 

  108. A. E. J. Wilson, Applications of photochromic polymer films, Phys. Technol., 15, 325–338 (1984).

    Google Scholar 

  109. H. G. Heller, New fatigue resistant organic photochromic materials, in: Fine Chemicals for the Electronics Industry (P. Bamfield, ed.), pp. 120–135, Royal Soc. Chem., London (1986).

    Google Scholar 

  110. V. Wintgens, L. J. Johnston, and J. C. Scaiano, Use of a photoreversible fulgide as an actinometer in one-and two-laser experiments, J. Am. Chem. Soc., 110, 511–517 (1988).

    Article  CAS  Google Scholar 

  111. C. Trundle and J. Brettle, Furyl fulgide as photochromic inks, PCT Int. Appl. WO, 8,801,288 (1988).

    Google Scholar 

  112. M. Hawkins and A. G. Bowyer, Furyl fulgide as inks for some printing, Eur. Pat. Appl. EP279600 (1988).

    Google Scholar 

  113. Y. Mitsuhashi, Saturable Fabry-Perot filter for nonlinear optical image processing, Opt. Lett., 6, 111–113 (1981).

    CAS  Google Scholar 

  114. L. H. Yu, Y. F. Ming, M. G. Fan, S. D. Yao, and N. Y. Lin, Synthesis and photochromism of aryl-substituted fulgides, Acta Chim. Sinica, 54, 716–721 (1996).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2002 Kluwer Academic Publishers

About this chapter

Cite this chapter

Fan, MG., Yu, L., Zhao, W. (2002). Fulgide Family Compounds: Synthesis, Photochromism, and Applications. In: Crano, J.C., Guglielmetti, R.J. (eds) Organic Photochromic and Thermochromic Compounds. Topics in Applied Chemistry. Springer, Boston, MA. https://doi.org/10.1007/0-306-46911-1_5

Download citation

  • DOI: https://doi.org/10.1007/0-306-46911-1_5

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-0-306-45882-8

  • Online ISBN: 978-0-306-46911-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics