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Crystal structures, two-photon absorption and theoretical calculation of a series of bis-vinylpyridine compounds synthesized by one-step solid state reaction

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Abstract

Three bis-vinylpyridine compounds (4,4′-bis(2-vinylpyridine)biphenyl L 1, 4,4′-bis(3-vinylpyridine) biphenyl L 2, and 4,4′-bis (4-vinylpyridine)biphenyl L 3) were synthesized by one-step solid-state reactions at room temperature, giving nearly quantitative yields. The compounds obtained were fully characterized by IR, MS and NMR spectroscopies. The structures of L 2 and L 3 were determined by single crystal X-ray diffraction analysis. No noticeable solvatochromism was observed in either one-photon absorption or one-photon excited fluorescence spectra. All of the compounds have high fluorescence quantum yields and long fluorescence lifetime. The linear and nonlinear optical properties of the compounds were investigated both experimentally and theoretically. Interestingly, the position of the nitrogen atom from pyridine influences their two-photon absorption across-sections.

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References

  1. Pond SJK, Rumi M, Levin MD, Park TC, Beljonne D, Day MW, Brédas JL, Marder SP, Perry JW. One- and two-photon spectroscopy of donor-acceptor-donor distyrylbenzene derivatives: Effect of cyano substitution and distortion from planarity. J Phys Chem A, 2002, 106: 11470–11480

    Article  CAS  Google Scholar 

  2. Abotto A, Beverina L, Bozio R, Facchetti A, Ferrante C, Pagani GA, Pedron D, Sigaorini R. Novel heterocycle-based two-photon absorbing dyes. Org Lett, 2002, 4: 1495–1498

    Article  Google Scholar 

  3. Olson CE, Previte MJR, Fourkas JT. Efficient and robust multiphoton data storage in molecular glasses and highly-crosslinked polymers. Nat Mater, 2002, 1: 225–228

    Article  CAS  Google Scholar 

  4. Fabbrini G, Menna E, Maggini M, Canazza A, Marcolongo G, Meneghetti M. Zinc-induced switching of the nonlinear optical properties of a functionalized bis(styryl)benzene. J Am Chem Soc, 2004, 126: 6238–6239

    Article  CAS  Google Scholar 

  5. Cumpston BH, Ananthavel SP, Barlow S, Dyer DL, Ehrlich JE, Erskine LL, Heikal AA, Kuebler SM, Lee IYS, McCordMaughon D, Qin J, Röckel H, Rumi M, Wu XL, Marder SR, Perry JW. Two-photon polymerization initiators for three-dimensional optical data storage and microfabrication. Nature, 1999, 398: 51–54

    Article  CAS  Google Scholar 

  6. Rumi M, Ehrlich JE, Heikal AA, Perry JW, Barlow S, Hu Z, Maughon DM, Parker TC, Rockel H, Thayumanavan S, Marder SR, Beljonne D, Bredas JL. Structure-property relationships for two-photon absorbing chromophores: Bis-donor diphenylpolyenes and bis(styryl)benzene derivatives. J Am Chem Soc, 2000, 122: 9500–9510

    Article  CAS  Google Scholar 

  7. Yan YX, Tao XT, Sun YH, Xu GB, Wang CK, Yang JX, Zhao X, Jiang MH. Synthesis, nonlinear optical properties and the possible mechanism of photopolymerization of two new two-photon absorption chromophores. J Solid State Chem, 2004, 177: 3007–3013

    Article  CAS  Google Scholar 

  8. Reinhardt BA, Brott LL, Clarson SJ, Dillardm AG, Bhatt JC, Kannan R, Yuanm L, He GS, Prasad PN. Highly active two-photon dyes: design, synthesis, and characterization toward application. Chem Mater, 1998, 10: 1863–1874

    Article  CAS  Google Scholar 

  9. Albota M, Beljonne D, Brédas JL, Ehrlich JE, Fu JY, Heikal AA, Hess SE, Kogej T, Levin MD, Marder SR, McCord-Maughon D, Perry JW, Röckel H, Rumi M, Subramaniam G, Webb WW, Wu XL, Xu C. Design of organic molecules with large two-photon absorption cross sections. Sience, 1998, 281: 1653–1656

    CAS  Google Scholar 

  10. Kim OK, Lee KS, Woo HY, Kim KS, He GS, Swiatkiewicz J, Prossad P. New class of two-photon-absorbing chromophores based on dithienothiophene. Chem Mater, 2000, 12: 284–286

    Article  CAS  Google Scholar 

  11. Ventelon L, Charier S, Moreaux L, Mertz J, Blanchard-Desce M. Nanoscale push-push dihydrophenanthrene derivatives as novel fluorophores for two-photon-excited fluorescence. Angew Chem Int Ed, 2001, 40: 2098–2101

    Article  CAS  Google Scholar 

  12. Chung SJ, Kim KS, Lin TC, He GS, Swiatkiewicz J, Prossad PN. Cooperative enhancement of two-photon absorption in multibranched structures. J Phys Chem B, 1999, 103: 10741–10745

    Article  CAS  Google Scholar 

  13. Cho BR, Son KH, Lee SH, Song YS, Lee YK, Jeon SJ, Choi JH, Lee H, Cho M. Two photon absorption properties of 1,3,5-tricyano-2,4,6-tris(styryl)benzene derivatives. J Am Chem Soc, 2001, 123: 10039–10045

    Article  CAS  Google Scholar 

  14. Abbotto A, Beverina L, Bozio R, Facchetti A, Ferrante C, Pagani GA, Pedron D, Signorini R. Novel heteroaromatic-based multi-branched dyes with enhanced two-photon absorption activity. Chem Commun, 2003, 2144–2145

  15. Wu J, Zhao YX, Li X, Shi MQ, Wu FP, Fang XY. Multibranched benzylidene cyclopentanone dyes with large two-photon absorption cross-sections. New J Chem, 2006, 30: 1098–1103

    Article  CAS  Google Scholar 

  16. Adronov A, Frchet JMJ, He GS, Kim KS, Chung SJ, Swiatkiewicz J, Prasad PN. Novel two-photon absorbing dendritic structures. Chem Mater, 2000, 12: 2838–2841

    Article  CAS  Google Scholar 

  17. Tian YP, Li L, Zhang JZ, Yang JX, Zhou HP, Wu JY, Sun PP, Tao LM, Guo YH, Wang CK, Xing H, Huang WH, Tao XT, Jiang MH. Investigations and facile synthesis of a series of novel multifunctional two-photon absorption materials. J Mater Chem, 2007, 34: 3646–3654

    Article  Google Scholar 

  18. Sun M, Wang P, Zhou HP, Yang JX, Wu JY, Tian YP, Tao XT, Jiang MH. 1D chain Cd(II) and Co(II) coordination polymers: Synthesis, crystal structures and luminescence properties. J Mol Struct, 2008, 873: 73–78

    Article  CAS  Google Scholar 

  19. Sumalekshmy S, Henary MM, Siegel N, Lawson PV, Wu Y, Schmidt K, Brédas J, Perry JW, Fahrni CJ. Design of emission ratiometric metal-ion sensors with enhanced two-photon cross section and brightness. J Am Chem Soc, 2007, 129: 11888–11889

    Article  CAS  Google Scholar 

  20. Sheldrick GM. SHELXTL V5.1 Software Reference Manual, Bruker AXS, Inc., Madison, Wisconsin, USA, 1997

    Google Scholar 

  21. Ganushchak NI, Prokopishin IY, Zyubrik AI. Reaction of p,p′-bis (diazonium diphenyl) chloride, diphenylmethane, and diphenyl oxide, sulfide, and sulfone with 2-vinylpyridine. L’vov. Gos. Univ., Lvov, USSR. Ukrainskii Khimicheskii Zhurnal Russ Ed, 1980, 46: 81–83

    CAS  Google Scholar 

  22. Shonfield PKA, Behrendt A, Jeffery JC, Maher JP, McCleverty JA, Psillakis E, Ward MD, Western C. Very weak electron-electron exchange interactions in paramagnetic dinuclear tris(pyrazolyl) boratomolybdenum centres with extended bridging ligands: Estimation of the exchange coupling constant J by simulation of second-order EPR spectra. Dalton Trans, 1999, 4341–4347

  23. Thompson ME, Anaheim C. Charge generators in heterolamellar multilayer thin films. PCT Int Appl, 1999, 1–80

  24. Snover JL, Byrd H, Suponeva EP, Vicenzi E, Thompson ME. growth and characterization of photoactive and electroactive zirconium bisphosphonate multilayer films. Chem Mater, 1996, 8: 1490–1499

    Article  CAS  Google Scholar 

  25. Hao FY, Zhang XJ, Tian YP, Zhou HP, Li L, Wu JY, Zhang SY, Yang JX, Jin BK, Tao XT, Zhou GY, Jiang MH. Design, crystal structures and enhanced frequency-upconverted lasing efficiencies of a new series of dyes from hybrid of inorganic polymers and organic chromophores. J Mater Chem, 2009, 19: 9163–9169

    Article  CAS  Google Scholar 

  26. Zhou HP, Li DM, Zhang JZ, Zhu YM, Wu JY, Hu ZJ, Yang JX, Xu GB, Tian YP, Xie Y, Tao XT, Jiang MH, Tao LM, Guo YH, Wang CK. Crystal structures, optical properties and theoretical calculation of novel two-photon polymerization initiators. Chem Phys, 2006, 322: 459–470

    Article  CAS  Google Scholar 

  27. Albota MA, Xu C, Webb WW. Two-photon fluorescece excitation cross sections of biomolecular probes from 690 to 960 nm. Appl Optics, 1998, 37: 7352–7356

    Article  CAS  Google Scholar 

  28. He GS, Tan LS, Zheng Q, Prasad PN. Multiphoton absorbing materials: Molecular designs, characterizations, and applications. Chem Rev, 2008, 108: 1245–1330

    Article  CAS  Google Scholar 

  29. Woo HY, Liu B, Kohler B, Korystov D, Mikhailovsky A, Bazan GC. Solvent effects on the two-photon absorption of distyrylbenzene chromophores. J Am Chem Soc, 2005, 127: 14721–14729

    Article  CAS  Google Scholar 

  30. Cronstrand P, Luo Y, Ågren H. Effects of dipole alignment and channel interference on two-photon absorption cross sections of two-dimensional charge-transfer systems. J Chem Phys, 2002, 117: 11102–11106

    Article  CAS  Google Scholar 

  31. Monson PR, McClain WM. Polarization dependence of the twophoton absorption of tumbling molecules with application of liquid 1-choronaphthalene and benzene. J Chem Phys, 1970, 53: 29–37

    Article  CAS  Google Scholar 

  32. Wenseleers W, Stellacci F, Meyer-Friedrichsen T, Mangel T, Marder SR, Perry JW. Five orders-of-magnitude enhancement of two-photon absorption for dyes on silver nanoparticle fractal clusters. J Phy Chem B, 2002, 106: 6853–6863

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Key Laboratory of Functional Inorganic Materials Chemistry of Anhui Province; Department of Chemistry, Anhui University, Hefei, 230039, China

    DongMei Li, Qiong Zhang, A. M. Showkot Hossain, Mei Sun, JieYing Wu, JiaXiang Yang, HongPing Zhou & YuPeng Tian

  2. Department of Physics, Shandong Normal University, Jinan, 250014, China

    LiMin Tao & ChuanKui Wang

  3. State Key Laboratory of Crystal Materials, Shandong University, Jinan, 250100, China

    YuPeng Tian

  4. State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, 210093, China

    YuPeng Tian

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  1. DongMei Li
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  2. Qiong Zhang
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  3. A. M. Showkot Hossain
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  4. Mei Sun
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  7. HongPing Zhou
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  8. LiMin Tao
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Correspondence to HongPing Zhou or YuPeng Tian.

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Li, D., Zhang, Q., Hossain, A.M.S. et al. Crystal structures, two-photon absorption and theoretical calculation of a series of bis-vinylpyridine compounds synthesized by one-step solid state reaction. Sci. China Chem. 54, 730–736 (2011). https://doi.org/10.1007/s11426-010-4141-6

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  • DOI: https://doi.org/10.1007/s11426-010-4141-6

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