Advertisement

Characterization of the one-electron oxidized Cu(II)-salen complexes with a side chain aromatic ring: the effect of the indole ring on the Cu(II)-phenoxyl radical species

  • Hiromi Oshita
  • Takayoshi Yoshimura
  • Seiji Mori
  • Fumito Tani
  • Yuichi ShimazakiEmail author
  • Osamu YamauchiEmail author
Original Paper
Part of the following topical collections:
  1. Special issue to celebrate the 80th birthday of Helmut Sigel

Abstract

To gain insights into the role of the proximal indole ring in the redox-active metal center as seen in galactose oxidase, we prepared the Cu(II)-salen-type complexes having a pendent indol-3-ylmethyl (1), methyl (2) or benzyl (3) group substituted on the ethylenediamine moiety and investigated the structures and redox properties by various physicochemical methods and theoretical calculations. Neutral complexes 1, 2, and 3 showed no significant difference in the UV–Vis–NIR and EPR spectra. One-electron oxidation of 1, 2, and 3 by addition of 1 equiv. of thianthrenyl radical gave [1]SbCl 6 , [2]SbCl 6 , and [3]SbCl 6 , respectively, which could be assigned to relatively localized phenoxyl radical species. The cyclic and differential pulse voltammograms of [1]SbCl 6 showed two redox waves with a large separation between the first and second redox potentials compared with the separations observed for [2]SbCl 6 and [3]SbCl 6 . This suggests that [1]SbCl 6 is more stabilized than [2]SbCl 6 and [3]SbCl 6 . The NIR band of [1]SbCl 6 showed a larger blue shift than that of [2]SbCl 6 and [3]SbCl 6 . The EPR spectrum of [2]SbCl 6 exhibited an intense signal at the g value of 2 due to partial disproportionation to form the EPR active two-electron oxidized complex [2] 2+ , while the EPR intensity of [1]SbCl 6 was much weaker than that of [2]SbCl 6 . These results indicate that the pendent indole moiety stabilizes the Cu(II)-phenoxyl radical in [1]SbCl 6 most probably by stacking with the phenoxyl moiety, which is further supported by DFT calculations.

Keywords

Cu(II)-salen complexes Phenoxyl radical Indole ring ππ Stacking Galactose oxidase 

Notes

Acknowledgements

We gratefully acknowledge the helpful discussions and suggestions by Prof. Dr. Hitoshi Abe, High Energy Accelerator Research Organization (KEK) and SOKENDAI (the Graduate University for Advanced Studies), Japan and Prof. Dr. Tatsuo Yajima, Kansai University, Japan. This work was supported in part by Grants-in-Aid for Scientific Research (Nos. 25410060 and 16K05716 to Y. S., and No. 15K05411 to S. M.) from the Ministry of +Education, Culture, Sports, Science, and Technology of Japan, and Cooperative Research Program of “Network Joint Research Center for Materials and Devices” (Institute for Materials Chemistry and Engineering, Kyushu University). This work was also supported by a Grant-in-Aid for Scientific Research on Innovative Areas “Precise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions” from MEXT, Japan (16H01001) to S. M. The generous allotment of computation time from the Research Center for Computational Science (RCCS), the National Institutes of Natural Sciences, Japan, is also gratefully acknowledged.

Supplementary material

775_2017_1508_MOESM1_ESM.pdf (652 kb)
Supplementary material 1 (PDF 651 kb)

References

  1. 1.
    Zhang M-Z, Chen Q, Yang G-F (2015) Eur J Med Chem 89:421–441CrossRefPubMedGoogle Scholar
  2. 2.
    Chadha N, Silakari O (2017) Eur J Med Chem 134:159–184CrossRefPubMedGoogle Scholar
  3. 3.
    Stubbe J, van der Donk WA (1998) Chem Rev 98:705–762CrossRefPubMedGoogle Scholar
  4. 4.
    Gray HB, Winkler JR (1996) Annu Rev Biochem 65:537–561CrossRefPubMedGoogle Scholar
  5. 5.
    Meyer EA, Castellano RK, Diederich F (2003) Angew Chem Int Ed 42:1210–1250CrossRefGoogle Scholar
  6. 6.
    Shih C, Museth AK, Abrahamsson M, Blanco-Rodriguez AM, Di Bilio AJ, Sudhamsu J, Crane BR, Ronayne KL, Towrie M, Vlček A, Richards JH, Winkler JR, Gray HB (2008) Science 320:1760–1762CrossRefPubMedGoogle Scholar
  7. 7.
    Takematsu K, Williamson H, Blanco-Rodríguez AM, Sokolová L, Nikolovski P, Kaiser JT, Towrie M, Clark IP, Vlček A Jr, Winkler JR, Gray HB (2013) J Am Chem Soc 135:15515–15525CrossRefPubMedGoogle Scholar
  8. 8.
    Wang J, Mauro JM, Edwards SL, Oatley SJ, Fishel LA, Ashford VA, Xuong N-H, Kraut J (1990) Biochemistry 29:7160–7173CrossRefPubMedGoogle Scholar
  9. 9.
    Poulos TM, Fenna RE (1994) In: Sigel H, Sigel A (eds) Metal ions in biological systems. Marcel Dekker, New York, vol 30, pp 25–75Google Scholar
  10. 10.
    Carredano E, Karlsson A, Kauppi B, Choudhury D, Parales RE, Parales JV, Lee K, Gibson DT, Eklund H, Ramaswamy S (2000) J Mol Biol 269:701–712CrossRefGoogle Scholar
  11. 11.
    Karlsson A, Parales JV, Parales RE, Gibson DT, Eklund H, Ramaswamy S (2003) Science 299:1039–1042CrossRefPubMedGoogle Scholar
  12. 12.
    Whittaker JW (2003) Chem Rev 103:2347–2363CrossRefPubMedGoogle Scholar
  13. 13.
    Ito N, Phillips SE, Stevens C, Ogel ZB, McPherson MJ, Keen JN, Yadav KD, Knowles PF (1991) Nature 350:87–90CrossRefPubMedGoogle Scholar
  14. 14.
    Rokhsana D, Howells AE, Dooley DM, Szilagyi RK (2012) Inorg Chem 51:3513–3524CrossRefPubMedGoogle Scholar
  15. 15.
    Ito N, Phillips SEV, Yadav KDS, Knowles PF (1994) J Mol Biol 238:704–814CrossRefGoogle Scholar
  16. 16.
    Baron AJ, Stevens C, Wilmot C, Seneviratne KD, Blakeley V, Dooley DM, Phillips SEV, Knowles PF, McPherson MJ (1994) J Biol Chem 269:25095–25105PubMedGoogle Scholar
  17. 17.
    Chaplin AK, Svistunenko DA, Hough MA, Wilson MT, Vijgenboom E, Worrall JAR (2017) Biochem J 474:809–825CrossRefPubMedGoogle Scholar
  18. 18.
    Nozaki Y, Tanford C (1971) J Biol Chem 246:2211–2217PubMedGoogle Scholar
  19. 19.
    Samanta U, Pal D, Chakrabarti P (1999) Acta Crystallogr Sect D 55:1421–1427CrossRefGoogle Scholar
  20. 20.
    Fischer BE, Sigel H (1980) J Am Chem Soc 102:2998–3008CrossRefGoogle Scholar
  21. 21.
    Scheller KH, Sigel H (1983) J Am Chem Soc 105:3005–3014CrossRefGoogle Scholar
  22. 22.
    Corfù NA, Sigel A, Operschall BP, Sigel H (2011) J Indian Chem Soc 88:1093–1115Google Scholar
  23. 23.
    Sigel A, Operschall BP, Sigel H (2014) J Biol Inorg Chem 19:691–703CrossRefPubMedGoogle Scholar
  24. 24.
    Yamauchi O, Odani A (1985) J Am Chem Soc 107:5938–5945CrossRefGoogle Scholar
  25. 25.
    Sugimori T, Masuda H, Ohata N, Koiwai K, Odani A, Yamauchi O (1997) Inorg Chem 36:576–583CrossRefGoogle Scholar
  26. 26.
    Yamauchi O, Odani A, Hirota S (2001) Bull Chem Soc Jpn 74:1525–1545CrossRefGoogle Scholar
  27. 27.
    Yamauchi O, Odani A, Takani M (2002) J Chem Soc, Dalton Trans 3411–3421.  https://doi.org/10.1039/B202385G
  28. 28.
    Shimazaki Y, Takani M, Yamauchi O (2009) Dalton Trans 7854–7869.  https://doi.org/10.1039/B905871K
  29. 29.
    Yamauchi O (2016) In: Jastrząb R, Tylkowski B (eds) New generation bioinorganic complexes. Walter de Gruyter, Berlin, pp 1–40Google Scholar
  30. 30.
    Shimazaki Y, Yajima T, Yamauchi O (2015) J Inorg Biochem 148:105–115CrossRefPubMedGoogle Scholar
  31. 31.
    Yamauchi O, Takani M, Toyoda K, Masuda H (1990) Inorg Chem 29:1856–1860CrossRefGoogle Scholar
  32. 32.
    Takani M, Takeda T, Yajima T, Yamauchi O (2006) Inorg Chem 45:5938–5946CrossRefPubMedGoogle Scholar
  33. 33.
    Shimazaki Y, Yajima T, Takani M, Yamauchi O (2009) Coord Chem Rev 253:479–492CrossRefGoogle Scholar
  34. 34.
    Iwatsuki S, Suzuki T, Yajima T, Shiraiwa T, Yamauchi O, Shimazaki Y (2011) Inorg Chim Acta 377:111–119CrossRefGoogle Scholar
  35. 35.
    Motoyama T, Shimazaki Y, Yajima T, Nakabayashi Y, Naruta Y, Yamauchi O (2004) J Am Chem Soc 126:7378–7385CrossRefPubMedGoogle Scholar
  36. 36.
    Rogers MS, Tyler EM, Akyumani N, Kurtis CR, Spooner RK, Deacon SE, Tamber S, Firbank SJ, Mahmoud K, Knowles PF, Phillips SEV, McPherson MJ, Dooley DM (2007) Biochemistry 46:4606–4618CrossRefPubMedPubMedCentralGoogle Scholar
  37. 37.
    Itoh S, Taki M, Fukuzumi S (2000) Coord Chem Rev 198:3–20CrossRefGoogle Scholar
  38. 38.
    Jazdzewski BA, Tolman WB (2000) Coord Chem Rev 200–202:633–685CrossRefGoogle Scholar
  39. 39.
    Chaudhuri P, Wieghardt K (2001) Prog Inorg Chem 50:151–216Google Scholar
  40. 40.
    Lyons CT, Stack TDP (2013) Coord Chem Rev 257:528–540CrossRefPubMedPubMedCentralGoogle Scholar
  41. 41.
    Shimazaki Y (2014) In: Zabicky J (ed) The chemistry of metal phenolates, vol 1. Wiley, Chichester, pp 593–668Google Scholar
  42. 42.
    Thomas F (2016) Dalton Trans 45:10866–10877CrossRefPubMedGoogle Scholar
  43. 43.
    Shimazaki Y, Yamauchi O (2011) Indian J Chem 50A:383–394Google Scholar
  44. 44.
    Pratt RC, Lyons CT, Wasinger EC, Stack TDP (2012) J Am Chem Soc 134:7367–7377CrossRefPubMedPubMedCentralGoogle Scholar
  45. 45.
    Verma P, Pratt RC, Storr T, Wasinger EC, Stack TDP (2011) Proc Natl Acad Sci 108:18600–18605CrossRefPubMedPubMedCentralGoogle Scholar
  46. 46.
    Perrin DD, Armarego WLF, Perrin DR (eds) (1966) Purification of laboratory chemicals. Pergamon Press, ElmsfordGoogle Scholar
  47. 47.
    Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson GA, Nakatsuji H, Li X, Caricato M, Marenich AV, Bloino J, Janesko BG, Gomperts R, Mennucci B, Hratchian HP, Ortiz JV, Izmaylov AF, Sonnenberg JL, Williams-Young, D, Ding F, Lipparini F, Egidi F, Goings J, Peng B, Petrone A, Henderson T, Ranasinghe D, Zakrzewski VG, Gao J, Rega N, Zheng G, Liang W, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Throssell K, Montgomery JA Jr, Peralta JE, Ogliaro F, Bearpark MJ, Heyd JJ, Brothers EN, Kudin KN, Staroverov VN, Keith TA, Kobayashi R, Normand J, Raghavachari K, Rendell AP, Burant JC, Iyengar SS, Tomasi J, Cossi M, Millam JM, Klene M, Adamo C, Cammi R, Ochterski JW, Martin RL, Morokuma K, Farkas O, Foresman JB, Fox DJ (2016) Gaussian16 Revision A.03, Gaussian Inc. Wallingford, CTGoogle Scholar
  48. 48.
    Yanai T, Tew DP, Handy NC (2004) Chem Phys Lett 393:51–57CrossRefGoogle Scholar
  49. 49.
    Grimme S, Antony J, Ehrlich S, Krieg H (2010) J Chem Phys 132:154104–154119CrossRefPubMedGoogle Scholar
  50. 50.
    Weigend F, Ahlrichs R (2005) Phys Chem Chem Phys 7:3297–3305CrossRefPubMedGoogle Scholar
  51. 51.
    Weigend F (2006) Phys Chem Chem Phys 8:1057–1065CrossRefPubMedGoogle Scholar
  52. 52.
    Tomasi J, Mennucci B, Cammi R (2005) Chem Rev 105:2999–3093CrossRefPubMedGoogle Scholar
  53. 53.
    Mulliken RS (1955) J Chem Phys 23:1833–1840CrossRefGoogle Scholar
  54. 54.
    Glendening ED, Reed AE, Carpenter JE, Weinhold F (1998) NBO Version 3.1Google Scholar
  55. 55.
    Johnson ER, Keinan S, Mori-Sánchez P, Contreras-Grarcía J, Cohen AJ, Yang W (2010) J Am Chem Soc 132:6498–6506CrossRefPubMedPubMedCentralGoogle Scholar
  56. 56.
    Contreras-Grarcía J, Johnson ER, Keinan S, Chaudret R, Piquemal J-P, Beratan DN, Yang W (2011) J Chem Theory Comput 7:625–632CrossRefGoogle Scholar
  57. 57.
    Poirier JM, Vottero C, Mieloszynski JL, Achour Z, Scheneuder M, Paquer D, Labat Y (1989) Sulfur Lett 10:169–173Google Scholar
  58. 58.
    Brunner H, Kroib R, Schemidt M (1985) Eur J Med Chem Chim Ther 21:333–338Google Scholar
  59. 59.
    Boduszek B, Shine HJ (1998) J Org Chem 53:5142–5143CrossRefGoogle Scholar
  60. 60.
    Connelly NG, Geiger WE (1996) Chem Rev 96:877–910CrossRefPubMedGoogle Scholar
  61. 61.
    Wang Y, Stack TDP (1996) J Am Chem Soc 118:13097–13098CrossRefGoogle Scholar
  62. 62.
    Wang Y, DuBois JL, Hedman B, Hodson KO, Stack TDP (1998) Science 279:537–540CrossRefPubMedGoogle Scholar
  63. 63.
    Chaudhuri P, Hess M, Flörke U, Wieghardt K (1998) Angew Chem Int Ed 37:2217–2220CrossRefGoogle Scholar
  64. 64.
    Chaudhuri P, Hess M, Weyhermuller T, Wieghardt K (1999) Angew Chem Int Ed 38:1095–1098CrossRefGoogle Scholar
  65. 65.
    Halcrow MA, Chia LML, Davies JE, Liu X, Yellowlees LJ, McInnes EJL, Mabbs FE (1998) Chem Commun 2465–2466.  https://doi.org/10.1039/A807076H
  66. 66.
    Itoh S, Taki M, Kumei H, Takayama S, Nagatomo S, Kitagawa T, Sakurada N, Arakawa R, Fukuzumi S (2000) Inorg Chem 39:3708–3711CrossRefPubMedGoogle Scholar
  67. 67.
    Shimazaki Y, Huth S, Hirota S, Yamauchi O (2002) Inorg Chim Acta 331:168–177CrossRefGoogle Scholar
  68. 68.
    Müller J, Weyhermüller T, Bill E, Hildebrandt P, Ould-moussa L, Glaser T, Wieghardt K (1998) Angew Chem Int Ed Engl 37:616–619CrossRefGoogle Scholar
  69. 69.
    Shimazaki Y, Huth S, Hirota S, Yamauchi O (2000) Bull Chem Soc Jpn 73:1187–1195CrossRefGoogle Scholar
  70. 70.
    Robin MB, Day P (1968) Adv Inorg Chem Radiochem 10:247–422CrossRefGoogle Scholar
  71. 71.
    Creutz C, Taube H (1969) J Am Chem Soc 91:3988–3989CrossRefGoogle Scholar
  72. 72.
    Hush NS (1967) In: Cotton FA (ed) Progress in inorganic chemistry, vol 8. Wiley, Chichester, pp 391–444CrossRefGoogle Scholar
  73. 73.
    Nelsen SF (2000) Chem Eur J 6:581–588CrossRefPubMedGoogle Scholar
  74. 74.
    Hush NS (1985) Coord Chem Rev 64:135–157CrossRefGoogle Scholar
  75. 75.
    Asami K, Tsukidate K, Iwatsuki S, Tani F, Karasawa S, Chiang L, Storr T, Thomas F, Shimazaki Y (2012) Inorg Chem 51:12450–12461CrossRefPubMedGoogle Scholar
  76. 76.
    Shimazaki Y, Arai N, Dunn TJ, Yajima T, Tani F, Ramogida CF, Storr T (2011) Dalton Trans 40:2469–2479CrossRefPubMedGoogle Scholar
  77. 77.
    D’Alessandro DM, Keene FR (2006) Chem Soc Rev 35:424–440PubMedGoogle Scholar
  78. 78.
    Yajima T, Takamido R, Shimazaki Y, Odani A, Nakabayashi Y, Yamauchi O (2007) Dalton Trans 3:299–307CrossRefGoogle Scholar
  79. 79.
    Shimazaki Y (2013) Adv Mat Phys Chem 3:60–71CrossRefGoogle Scholar
  80. 80.
    Orio M, Jarjayes O, Kanso H, Philouze C, Neese F, Thomas F (2010) Angew Chem Int Ed 122:5109–5112CrossRefGoogle Scholar
  81. 81.
    Asami K, Takashina A, Kobayashi M, Iwatsuki S, Yajima T, Kochem A, van Gastel M, Tani F, Kohzuma T, Thomas F, Shimazaki Y (2014) Dalton Trans 43:2283–2293CrossRefPubMedGoogle Scholar
  82. 82.
    Oshita H, Kikuchi M, Mieda K, Ogura T, Yoshimura T, Tani F, Yajima T, Abe H, Mori S, Shimazaki Y (2017) Chem Select 2:10221–10231Google Scholar

Copyright information

© SBIC 2017

Authors and Affiliations

  • Hiromi Oshita
    • 1
  • Takayoshi Yoshimura
    • 1
  • Seiji Mori
    • 1
    • 2
  • Fumito Tani
    • 3
  • Yuichi Shimazaki
    • 2
    Email author
  • Osamu Yamauchi
    • 4
    • 5
    Email author
  1. 1.Graduate School of Science and EngineeringIbaraki UniversityMitoJapan
  2. 2.College of ScienceIbaraki UniversityMitoJapan
  3. 3.Institute for Materials Chemistry and EngineeringKyushu UniversityFukuokaJapan
  4. 4.Faculty of Chemistry, Materials and BioengineeringKansai UniversitySuitaJapan
  5. 5.Department of Chemistry, Graduate School of ScienceNagoya UniversityNagoyaJapan

Personalised recommendations