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Substituent effects in the tuning of excited-state intramolecular proton transfer and optical properties of the derivatives of 2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole

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Abstract

The intramolecular proton transfer process and optical properties of a series of derivatives of 2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole (HOXD) have been studied. The effects of electron-donating and -withdrawing substituents on the intramolecular proton transfer and optical properties in the S0 and S1 states have been investigated to find out the relationships between them and the Hammett substituent constants (δ p). The statistically valid linear correlations are observed between the δ p and the ionization potential (IP), electron affinity (EA), the relative energies (ΔE) and the direct energy barriers (ΔE d) of the intramolecular proton transfer reactions, and the optical properties of HOXD and its substituted derivatives. The λ abs, λ fl, and λ ph of the electron-withdrawing substituted derivatives have bathochromic shifts, while the corresponding values of the electron-donating substituted derivatives show hypsochromic shifts compared with the parent compound HOXD. A successful tuning in the emission color was achieved: the emission wavelength was substituent δ p dependent, providing a powerful strategy for predicting the optical properties of novel electroluminophores.

Graphical Abstract

The effects of substituents on the intramolecular proton transfer and optical properties for 2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole and its diverse derivatives have been theoretically investigated with the aim to get the relationships between the ESIPT reactions, optical properties, and the Hammett substituent constants (δ p).

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References

  1. Chen C-L, Lin C-W, Hsieh C-C, Lai C-H, Lee G-H, Wang C-C, Chou P-T (2009) J Phys Chem A 113:205

    Article  CAS  Google Scholar 

  2. Park S, Seo J, Kim SH, Park SY (2008) Adv Funct Mater 18:726

    Article  CAS  Google Scholar 

  3. Nosenko Y, Wiosna-Sałyga G, Kunitski M, Petkova I, Singh A, Buma WJ, Thummel RP, Brutschy B, Waluk J (2008) Angew Chem Int Ed Engl 47:6037

    Article  CAS  Google Scholar 

  4. Migani A, Bearpark MJ, Olivucci M, Robb MA (2007) J Am Chem Soc 129:3703

    Article  CAS  Google Scholar 

  5. Shynkar VV, Klymchenko AS, Kunzelmann C, Duportail G, Muller CD, Demchenko AP, Freyssinet J-M, Mely Y (2007) J Am Chem Soc 129:2187

    Article  CAS  Google Scholar 

  6. Wu Y, Peng X, Fan J, Gao S, Tian M, Zhao J, Sun S (2007) J Org Chem 72:62

    Article  CAS  Google Scholar 

  7. Henary MM, Wu Y, Cody J, Sumalekshmy S, Li J, Mandal S, Fahrni CJ (2007) J Org Chem 72:4784

    Article  CAS  Google Scholar 

  8. Qian Y, Li S, Zhang G, Wang Q, Wang S, Xu H, Li C, Li Y, Yang G (2007) J Phys Chem B 111:5861

    Article  CAS  Google Scholar 

  9. Sakota K, Inoue N, Komoto Y, Sekiya H (2007) J Phys Chem A 111:4596

    Article  CAS  Google Scholar 

  10. Strandjord AJG, Courtney SH, Friedrich DM, Barbara PF (1983) J Phys Chem 87:1125

    Article  CAS  Google Scholar 

  11. McMorrow D, Kasha M (1984) J Phys Chem 88:2235

    Article  CAS  Google Scholar 

  12. Schwartz BJ, Peteanu LA, Harris CB (1992) J Phys Chem 96:3591

    Article  CAS  Google Scholar 

  13. Sengupta PK, Kasha M (1979) Chem Phys Lett 68:382

    Article  CAS  Google Scholar 

  14. Das K, Sarkar N, Ghosh AK, Majumdar D, Nath DN, Bhattacharyya K (1994) J Phys Chem 98:9126

    Article  CAS  Google Scholar 

  15. Douhal A, Lahmani F, Zewail AH (1996) Chem Phys 207:477

    Article  CAS  Google Scholar 

  16. Douhal A, Lahmani F, Zehnacker-Rentien A (1993) Chem Phys 178:493

    Article  CAS  Google Scholar 

  17. Sytnik A, Kasha M (1994) Proc Natl Acad Sci USA 91:8627

    Article  CAS  Google Scholar 

  18. Liang F, Wang L, Ma D, Jing X, Wang F (2002) Appl Phys Lett 81:4

    Article  CAS  Google Scholar 

  19. Tong H, Zhou G, Wang L, Jing X, Wang F, Zhang J (2003) Tetrahedron Lett 44:131

    Article  CAS  Google Scholar 

  20. Brunner K, Dijken AV, Börner H, Bastiaansen JJAM, Kiggen NMM, Langeveld BMW (2004) J Am Chem Soc 126:6035

    Article  CAS  Google Scholar 

  21. Yi Y, Zhu L, Shuai Z (2008) Macromol Theory Simul 17:12

    Article  CAS  Google Scholar 

  22. Parthenopoulos DA, McMorrow D, Kasha M (1991) J Phys Chem 95:2668

    Article  CAS  Google Scholar 

  23. Ma D, Liang F, Wang L, Lee ST, Hung L (2002) Chem Phys Lett 358:24

    Article  CAS  Google Scholar 

  24. Keck J, Kramer HEA, Port H, Hirsch T, Fischer P, Rytz G (1996) J Phys Chem 100:14468

    Article  CAS  Google Scholar 

  25. Douhal A, Sastre R (1994) Chem Phys Lett 219:91

    Article  CAS  Google Scholar 

  26. Photochromism: memories and switches (2000) Special issue of Chem Rev 100

  27. Doroshenko AO, Posokhov EA, Verezubova AA, Ptyagina LM (2000) J Phys Org Chem 13:253

    Article  CAS  Google Scholar 

  28. Doroshenko AO, Posokhov EA, Verezubova AA, Ptyagina LM, Skripkina VT, Shershukov VM (2002) Photochem Photobiol Sci 1:92

    Article  CAS  Google Scholar 

  29. Gaenko AV, Devarajan A, Tselinskii IV, Ryde U (2006) J Phys Chem A 110:7935

    Article  CAS  Google Scholar 

  30. Tamoto N, Adachi C, Nagai K (1997) Chem Mater 9:1077

    Article  CAS  Google Scholar 

  31. Uchida M, Adachi C, Koyama T, Taniguchi Y (1999) J Appl Phys 86:1680

    Article  CAS  Google Scholar 

  32. Wang JF, Jabbour GE, Mash EA, Anderson J, Zhang Y, Lee PA, Armstrong NR, Peyghambarian N, Kippelen B (1999) Adv Mater 11:1266

    Article  CAS  Google Scholar 

  33. Kido J, Hayase H, Hongawa K, Nagai K, Okuyama K (1994) Appl Phys Lett 65:2124

    Article  CAS  Google Scholar 

  34. Antoniadis H, Inbasekaran M, Woo EP (1998) Appl Phys Lett 73:3055

    Article  CAS  Google Scholar 

  35. Hu Y, Zhang Y, Liang F, Wang L, Ma D, Jing X (2003) Synth Met 137:1123

    Article  CAS  Google Scholar 

  36. Yang Z, Yang S, Zhang J (2007) J Phys Chem A 111:6354

    Article  CAS  Google Scholar 

  37. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JAJ, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, revision C.02. Gaussian Inc, Wallingford

  38. Foresman JB, Head-Gordon M, Pople JA, Frisch MJ (1992) J Phys Chem 96:135

    Article  CAS  Google Scholar 

  39. Dreuw A, Head-Gordon M (2005) Chem Rev 105:4009

    Article  CAS  Google Scholar 

  40. Barone V, Polimeno A (2007) Chem Soc Rev 36:1724

    Article  CAS  Google Scholar 

  41. Jacquemin D, Perpete EA, Ciofini I, Adamo C (2009) Acc Chem Res 42:326

    Article  CAS  Google Scholar 

  42. Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785

    Article  CAS  Google Scholar 

  43. Sun M, Niu B, Zhang J (2008) J Mol Struct: Theochem 862:85

    Article  CAS  Google Scholar 

  44. Sun M, Niu B, Zhang J (2008) Theor Chem Acc 119:489

    Article  CAS  Google Scholar 

  45. Gahungu G, Zhang J (2005) J Mol Struct: Theochem 755:19

    Article  CAS  Google Scholar 

  46. Li Z, Zhang J (2006) Chem Phys 331:159

    Article  CAS  Google Scholar 

  47. Domingo LR, Picher MT, Zaragozá RJ (1998) J Org Chem 63:9183

    Article  CAS  Google Scholar 

  48. Shukla MK, Leszczynski J (2005) Int J Quantum Chem 105:387

    Article  CAS  Google Scholar 

  49. Halls MD, Schlegel HB (2001) Chem Mater 13:2632

    Article  CAS  Google Scholar 

  50. Zhang J, Frenking G (2004) J Phys Chem A 108:10296

    Article  CAS  Google Scholar 

  51. Zhang J, Frenking G (2004) Chem Phys Lett 394:120

    Article  CAS  Google Scholar 

  52. Gahungu G, Zhang J (2005) J Phys Chem B 109:17762

    Article  CAS  Google Scholar 

  53. Gahungu G, Zhang J (2005) Chem Phys Lett 410:302

    Article  CAS  Google Scholar 

  54. Hu B, Gahungu G, Zhang J (2007) J Phys Chem A 111:4965

    Article  CAS  Google Scholar 

  55. Ahlrichs R, Bär M, Häser M, Horn H, Kälmel C (1989) Chem Phys Lett 162:165

    Article  CAS  Google Scholar 

  56. Santos L, Vargas A, Moreno M, Manzano BR, Lluch JM, Douhal A (2004) J Phys Chem A 108:9331

    Article  CAS  Google Scholar 

  57. Hammett LP (1937) J Am Chem Soc 59:96

    Article  CAS  Google Scholar 

  58. Hansch C, Leo A, Taft RW (1991) Chem Rev 91:165

    Article  CAS  Google Scholar 

  59. Wheeler SE, Houk KN (2008) J Am Chem Soc 130:10854

    Article  CAS  Google Scholar 

  60. Romero FA, Hwang I, Boger DL (2006) J Am Chem Soc 128:14004

    Article  CAS  Google Scholar 

  61. Zdilla MJ, Dexheimer JL, Abu-Omar MM (2007) J Am Chem Soc 129:11505

    Article  CAS  Google Scholar 

  62. Pohl R, Anzenbacher P Jr (2003) Org Lett 5:2769

    Article  CAS  Google Scholar 

  63. Pohl R, Montes VA, Shinar J, Anzenbacher P Jr (2004) J Org Chem 69:1723

    Article  CAS  Google Scholar 

  64. Pan Y, Fu Y, Liu S, Yu H, Gao Y, Guo Q, Yu S (2006) J Phys Chem A 110:7316

    Article  CAS  Google Scholar 

  65. Zhang X, Wang C-J, Liu L-H, Jiang Y-B (2002) J Phys Chem B 106:12432

    Article  CAS  Google Scholar 

  66. Fayet G, Joubert L, Rotureau P, Adamo C (2008) J Phys Chem A 112:4054

    Article  CAS  Google Scholar 

  67. Cleij TJ, King JK, Jenneskens LW (2000) Macromolecules 33:89

    Article  CAS  Google Scholar 

  68. Jacquemin D, Champagne B, André J-M (1996) Synth Met 80:205

    Article  CAS  Google Scholar 

  69. Sugiyama K, Yoshimura D, Miyamae T, Miyazaki T, Ishii H, Ouchi Y, Seki K (1998) J Appl Phys 83:4928

    Article  CAS  Google Scholar 

  70. Jena NR, Mishra PC (2005) J Phys Chem B 109:14205

    Article  CAS  Google Scholar 

  71. Kasha M, Heldt J, Gormin D (1995) J Phys Chem 99:7281

    Article  CAS  Google Scholar 

  72. Cossi M, Rega N, Scalmani G, Barone V (2003) J Comput Chem 24:669

    Article  CAS  Google Scholar 

  73. Cossi M, Barone V (2001) J Chem Phys 115:4708

    Article  CAS  Google Scholar 

  74. Aquino AJA, Lischka H, Hattig C (2005) J Phys Chem A 109:3201

    Article  CAS  Google Scholar 

  75. Joachain CJ, Brandsen BH (1983) Physics of atoms and molecules. Longman, London

    Google Scholar 

  76. Köse ME, Mitchell WJ, Kopidakis N, Chang CH, Shaheen SE, Kim K, Rumbles G (2007) J Am Chem Soc 129:14257

    Article  CAS  Google Scholar 

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Acknowledgments

Financial supports from the NSFC (Nos. 50873020, 20773022), the NCET-06-0321, and the NENU-STB-07-007 are gratefully acknowledged.

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Authors and Affiliations

  1. Faculty of Chemistry, Northeast Normal University, Changchun, 130024, China

    Ruifa Jin & Jingping Zhang

  2. Department of Chemistry, Chifeng University, Chifeng, 024000, China

    Ruifa Jin

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  1. Ruifa Jin
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  2. Jingping Zhang
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Correspondence to Jingping Zhang.

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Jin, R., Zhang, J. Substituent effects in the tuning of excited-state intramolecular proton transfer and optical properties of the derivatives of 2-(2-hydroxyphenyl)-5-phenyl-1,3,4-oxadiazole. Theor Chem Acc 124, 331–338 (2009). https://doi.org/10.1007/s00214-009-0613-1

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