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Conformational analysis of 2-anthryl-ethylene derivatives: Photochemical and computational investigation

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Abstract

2-Anthrylethylene derivatives 1 E5 E and 1 Z are synthesized to study the cis-trans photoisomerization. Interestingly, unlike 9-anthrylethylene derivatives, 2-anthrylethylene derivatives 1 E to 5 E do not exhibit E(trans) to Z (cis) photoisomerization upon direct and triplet sensitization. One-way Z (cis) to E (trans) photoisomerization of 1 Z is found to be very efficient under direct and triplet sensitization conditions, demonstrating the involvement of both singlet and triplet states. 1 E5 E exhibits excitation wavelength dependent fluorescence indicating the existence of conformers (rotamers) at room temperature, which is confirmed by fluorescence lifetimes measurements of compounds 1 E and 2 E. Theoretical studies are carried out at DFT and ab initio methodology and the calculated relative energy difference of the conformers is very small; it ranges between 2.9 kJ·mol−1 to 6.3 kJ·mol−1 for both ground and excited states.

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References

  1. G. S. Hammond, J. Saltiel, A. A. Lamola, N. J. Turro, J. S. Bradshaw, D. O. Cowan, R. C. Counsell, V. Vogt, and C. Dalton, J. Am. Chem. Soc., 86, 3197–3217 (1964).

    Article  CAS  Google Scholar 

  2. H. A. Hammond, D. E. DeMeyer, and J. L. R. Williams, J. Am. Chem. Soc., 91, 5180/5181 (1969).

    Google Scholar 

  3. D. H. Waldeck, Chem. Rev., 91, 415–436 (1991).

    Article  CAS  Google Scholar 

  4. H. Gorner and H. Kuhn, J. Adv. Photochem., 19, 1–117 (1995).

    Google Scholar 

  5. J. Saltiel and Y. P. Sun, Eds. Photochromism, Molecular Systems, Elsevier, Amsterdam (1990).

    Google Scholar 

  6. A. J. Merer and R. S. Mulliken, Chem. Rev., 69, 639–656 (1969).

    Article  CAS  Google Scholar 

  7. R. S. Mulliken, J. Chem. Phys., 66, 2448–2451 (1977).

    Article  CAS  Google Scholar 

  8. H. Meier, Angew. Chem., Int. Ed. Eng., 31, 1399–1420 (1992).

    Article  Google Scholar 

  9. A. Simeonov, M. Matsuhita, E. A. Juban, E. H. Z. Thompson, T. Z. Hoffmann, A. E. Beuscher IV, M. J. Taylor, Peter Wirsching, Wolfgang Rettig, J. K. Mc Cusker, R. C. Stevens, D. P. Miller, P. G. Schultz, R. A. Lerner, and K. D. Janda, Science, 290, 307–313 (2000).

    Article  CAS  Google Scholar 

  10. V. Papper and G. I. Likhtenshtein, J. Photochem. Photobiol A, 140, 39–52 (2001).

    Article  CAS  Google Scholar 

  11. J. Saltiel, T. S. R. Krishna, and A. M. Turek, J. Am. Chem. Soc., 127, 6938/6939 (2005).

    Google Scholar 

  12. K. Akiu, M. Saijo, M. Ikegami, and T. Arai, Bull. Chem. Soc. Jpn., 78, 1132–1137 (2005).

    Article  CAS  Google Scholar 

  13. A. Momotake and T. Arai, J. Photochem. Photobiol. C, 5, 1–25 (2004).

    Article  CAS  Google Scholar 

  14. J. C. Roberts and J. A. Pincock, J. Org. Chem., 71, 1480–1492 (2006).

    Article  CAS  Google Scholar 

  15. J. S. Yang, K. L. Liau, C. W. Tu, and C. Y. Hwang, J. Phys. Chem. A, 109, 6450–6456 (2005).

    Article  CAS  Google Scholar 

  16. M. Uda, A. Momotake, and T. Arai, Tetrahedron Lett., 46, 3021–3024 (2005).

    Article  CAS  Google Scholar 

  17. D. I. Schuster, B. Nuber, S. A. Vail, S. MacMahon, C. Lin, S. R. Wilson, and A. Khong, Photochem. Photobiol. Sci., 2, 315–321 (2003).

    Article  CAS  Google Scholar 

  18. H. Tatewaki, N. Baden, A. Momotake, T. Arai, and M. Terazima, J. Phys. Chem. B, 108, 12783–12789 (2004).

    Article  CAS  Google Scholar 

  19. N. J. Turro, Modern Molecular Photochemistry, The Benzamin, Cummings Publishing Co., Inc., Menlo Park (C.A)-London, Amsterdam (1978).

    Google Scholar 

  20. J. Saltiel and J. L. Charlton, in Rearrangement in Ground, Excited States, P. deMayo (ed.), Academic Press, New York (1980), 3, p. 25.

    Google Scholar 

  21. Kirk-Othner Encyclopedia of Chemical Technology. 4th ed. Willey (1996), 3, p. 25.

  22. B. L. Feringa, Tetrahedron, 94, 8267–8310 (1993).

    Article  Google Scholar 

  23. A. M. Braun, M. J. Maurette, and E. Oliveros, Photochemical Technology, Wiley, New York (1991).

    Google Scholar 

  24. B. L. Feringa, R. A. van Delden, N. Koumura, and E. M. Geertsema, Chem. Rev., 100, 1789–1816 (2000).

    Article  CAS  Google Scholar 

  25. V. Balogh-Nair and K. Nakanishi, in: Chemistry, Biology of Synthetic Retenoids, M. Dawson and W. Okamura (eds.), CRC Press, Boca-Ranton (1990), FL, 147.

    Google Scholar 

  26. V. J. Rao, F. Derguini, K. Nakanishi, T. Taguchi, A. Hosada, Y. Hanzawa, T. Kobayashi, C. M. Pande, and R. R. Callender, J. Am. Chem. Soc., 108, 6077/6078 (1986).

    Google Scholar 

  27. R. S. H. Liu and Y. Shichida, in: Photochemistry in Organized, Constrained Media, V. Ramamurthy (ed.), VCH Publishers, Chapter 18, New York (1991).

  28. M. Irie, Chem. Rev., 100, 1685–1716 (2000).

    Article  CAS  Google Scholar 

  29. T. Arai, T. Karatsu, H. Sakuragi, and K. Tokumari, Tetrahedron Lett., 24, 2873–2876 (1983).

    Article  CAS  Google Scholar 

  30. H. Hamaguchi, M. T. Karatsu, T. Arai, and K. Tokumaru, J. Am. Chem. Soc., 108, 1698/1699 (1986).

    Google Scholar 

  31. T. Arai and K. Tokumaru, Chem. Rev., 93, 23–39 (1993).

    Article  CAS  Google Scholar 

  32. H. D. Becker, Chem. Rev., 93, 145–172 (1993).

    Article  CAS  Google Scholar 

  33. J. Saltiel, N. Tarkalanov, and D. F. Sears Jr., J. Am. Chem. Soc., 117, 5586/5587 (1995).

    Google Scholar 

  34. J. Saltiel, Y. Zhang, and D. F. Sears Jr., J. Am. Chem. Soc., 118, 2811–2817 (1996).

    Article  CAS  Google Scholar 

  35. J. Saltiel, Y. Zhang, and D. F. Sears Jr., J. Am. Chem. Soc., 119, 11202–11210 (1997).

    Article  CAS  Google Scholar 

  36. J. Saltiel, G. Krishnamoorthy, and D. F. Sears Jr., Photochem. Photobiol. Sci., 2, 1162–1168 (2003).

    Article  CAS  Google Scholar 

  37. F. D. Lewis and X. Liu, J. Am. Chem. Soc., 121, 11928/11929 (1999).

    Google Scholar 

  38. U. Mazzucato and F. Momicchioli, Chem. Rev., 91, 1679–1719 (1991).

    Article  CAS  Google Scholar 

  39. G. Fischer and E. Fischer, J. Phys. Chem., 85, 2611–2613 (1981).

    Article  CAS  Google Scholar 

  40. A. Spalletti, G. Bartocci, F. Masetti, U. Mazzucato, and G. Cruciani, Chem. Phys., 160, 131–144 (1992).

    Article  CAS  Google Scholar 

  41. G. Bartocci, U. Mazzucato, and A. Spalletti, Chem. Phys., 202, 367–376 (1996).

    Article  CAS  Google Scholar 

  42. K. P. Ghiggino, P. F. Skilton, and E. Fischer, J. Am. Chem. Soc., 108, 1146–1149 (1986).

    Article  CAS  Google Scholar 

  43. T. Wismontski-Knittel, P. K. Das, and E. Fischer, J. Phys. Chem., 88, 1163–1168 (1984).

    Article  CAS  Google Scholar 

  44. T. Arai, T. Karatsu, H. Sakuragi, K. Tokumaru, N. Tamai, and I. Yamazaki, Chem. Phys. Lett., 158, 429–434 (1989).

    Article  CAS  Google Scholar 

  45. T. J. Kang, T. Etheridge, W. Jarzeba, and P. F. Barbara, J. Phys. Chem., 93, 1876–1881 (1989).

    Article  CAS  Google Scholar 

  46. A. M. Brearley, A. J. G. Strandjord, S. R. Flom, and P. F. Barbara, Chem. Phys. Lett., 113, 43–48 (1985).

    Article  CAS  Google Scholar 

  47. T. Karatsu, N. Yoshikawa, A. Kitamura, and K. Tokumaru, Chem. Lett., 381–384 (1994).

  48. V. Krongauz, N. Castel, and E. Fischer, J. Photochem., 39, 285–300 (1987).

    Article  CAS  Google Scholar 

  49. T. Karatsu, H. Itoh, A. Nishigaki, K. Fukui, A. Kitamura, S. Matsuo, and H. Misawa, J. Phys. Chem. A, 104, 6993–7003 (2000).

    Article  CAS  Google Scholar 

  50. H. J. Jacobs and E. Havinga, Adv. Photochem., 11, 305 (1979).

    CAS  Google Scholar 

  51. J. B. Birks, G. Bartocci, G. G. Aloisi, S. Dellonte, and F. Barigelletti, Chem. Phys., 51, 113–120 (1980).

    Article  CAS  Google Scholar 

  52. G. Bartocci, G. Ginocchietti, U. Mazzucato, and A. Spalletti, Chem. Phys., 328, 275–283 (2006).

    Article  CAS  Google Scholar 

  53. N. Marcotte and S. Fery-Forgues, J. Photochem. Photobiol. A: Chemistry, 130, 133–138 (2000).

    Article  CAS  Google Scholar 

  54. G. Bartocci and A. Spalletti, J. Phys. Chem. A, 106, 7068 (2002).

    Article  CAS  Google Scholar 

  55. S. Ciorba, F. Fontana, G. Ciancaleoni, T. Caronna, U. Mazzucato, and A. Spalletti, J. Fluorescence, 19, 759 (2009).

    Article  CAS  Google Scholar 

  56. G. Bartocci, G. Galiazzo, G. Ginocchietti, U. Mazzucato, and A. Spalletti, Photochem. Photobiol. Sci., 3, 870 (2004).

    Article  CAS  Google Scholar 

  57. G. Ginocchietti, G. Galiazzo, U. Mazzucato, and A. Spalletti, Photochem. Photobiol. Sci., 4, 547 (2005).

    Article  CAS  Google Scholar 

  58. I. Barldi, E. Benassi, and A. Spalletti, Spectrochim. Acta Part A: Molecular, Biomolecular Spectroscopy, 71, 543 (2008).

    Article  Google Scholar 

  59. K. M. Bushan, G. V. Rao, T. Soujanya, V. J. Rao, S. Saha, and A. Samanta, J. Org. Chem., 66, 681–688 (2001).

    Article  CAS  Google Scholar 

  60. M. J. R. Reddy, G. V. Rao, K. Manibhushan, M. J. R. Reddy, V. R. Gopal, and V. J. Rao, Chem. Lett., 3, 186/187 (2001).

    Google Scholar 

  61. M. J. R. Reddy, U. Srinivas, K. Srinivas, V. V. Reddy, and V. J. Rao, Bull. Chem. Soc. Jpn., 75, 2487–2495 (2002).

    Article  CAS  Google Scholar 

  62. V. R. Gopal, A. M. Reddy, and V. J. Rao, J. Org. Chem., 60, 7966–7973 (1995).

    Article  CAS  Google Scholar 

  63. P. F. Barbara and W. Jarzeba, Adv. Photochem., 15, 1 (1990).

    CAS  Google Scholar 

  64. E. Z. Lippert, W. Rettig, V. Banacic-Koutecky, F. Heisel, and J. Meihe, Adv. Chem. Phys., 68, 1 (1987).

    CAS  Google Scholar 

  65. J. C. Scaiano, Handbook of Organic Photochemistry; CRC press, Boca Raton, FL, 1 (1989).

    Google Scholar 

  66. J. G. Calvert and J. N. Pitts Jr., in: Photochemistry, Eds, Wiley, Chapter VII, New York (1966).

  67. K. Tanaka, T. Miura, N. Umezawa, Y. Urano, K. Kikuchi, T. Higuchi, and T. Nagano, J. Am. Chem. Soc., 123, 2530–2536 (2001).

    Article  CAS  Google Scholar 

  68. A. Fairbourne, J. Chem. Soc., 119, 1573–1582 (1921).

    Article  CAS  Google Scholar 

  69. J. T. Traxler, Syn. Comm., 7, 161–166 (1977).

    Article  CAS  Google Scholar 

  70. P. H. Gore, J. Chem. Soc., 1616–1618 (1959).

  71. J. A. Marshall, N. H. Anderson, and J. W. Schlicher, J. Org. Chem., 35, 858–861 (1970).

    Article  CAS  Google Scholar 

  72. W. S. Wadsworth, Org. React., 25, 73–145 (1977).

    CAS  Google Scholar 

  73. B. E. Maryanoff and A. B. Reitz, Chem. Rev., 89, 863–927 (1989).

    Article  CAS  Google Scholar 

  74. A. M. Reddy, V. R. Gopal, and V. J. Rao, Ind. J. Chem., 35B, 312–317 (1996).

    CAS  Google Scholar 

  75. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian 03, Revision B.01, Gaussian, Inc., Wallingford CT (2004).

    Google Scholar 

  76. G. Bartocci, U. Masetti, U. Mazzucato, A. Spalletti, G. Orlandi, and G. Poggi, J. Chem. Soc., Faraday Trans., 84, 385–399 (1988).

    Article  CAS  Google Scholar 

  77. F. Momicchioli, I. Baraldi, and E. Fischer, J. Photochem. Photobiol A, 48, 95–107 (1989).

    Article  CAS  Google Scholar 

  78. C. Reichhardt, Solvents, Solvent Effects in Organic Chemistry, VCH, Weinhein (1988).

    Google Scholar 

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Correspondence to Kolupula Srinivas.

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Original Russian Text Copyright © 2012 by U. Srinivas, P. Arun Kumar, Kolupula Srinivas, K. Bhanuprakash, V. Jayathirtha Rao

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 53, No. 5, pp. 872–886, September–October, 2012.

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Srinivas, U., Arun Kumar, P., Srinivas, K. et al. Conformational analysis of 2-anthryl-ethylene derivatives: Photochemical and computational investigation. J Struct Chem 53, 851–865 (2012). https://doi.org/10.1134/S0022476612050058

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