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Influence of Hydrogen Bonding and Polarity on the Spectral Properties of 4-Aminophthalimide Clusters Formed with Triethylamine and Dimethyl Sulfoxide in Solution

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Abstract

The time-dependent density functional theory (TDDFT) method has been carried out to study the influences of hydrogen bonding and solvent polarity on the spectral properties of 4-aminophthalimide (4AP) clusters formed with hydrogen-accepting solvents triethylamine (TEA) and dimethyl sulfoxide (DMSO). The ground- and S1-state geometry structure optimizations, hydrogen bond energies, absorption and emission spectra for both the 4AP monomer and its two triply hydrogen-bonded clusters 4AP + (TEA)3 and 4AP + (DMSO)3 have been calculated using DFT and TDDFT methods respectively with the hybrid exchange correlation functional PBE1PBE and split-valence basis set 6-311++G(d,p). It has been demonstrated that the two hydrogen bonds I and II formed with the amine group of 4AP are significantly strengthened while the hydrogen bond III formed with the imide group is slightly weakened due to the intramolecular charge transfer from the amine group to the two carbonyl groups of the 4AP molecule upon photoexcitation. In addition, the hydrogen bonds formed by 4AP with DMSO are stronger than those formed with TEA, which together with its strong polarity, should be the main reasons for the more redshifts of both the absorption and the fluorescence spectra of 4AP in solvent DMSO than those in TEA.

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References

  1. P. F. McGarry, S. Jockusch, Y. Fujiwara, N. A. Kaprinidis, and N. J. Turro (1997). J. Phys. Chem. A 101, 764.

    Article  CAS  Google Scholar 

  2. K.-L. Han and G.-J. Zhao Hydrogen Bonding and Transfer in the Excited State (Wiley, Chichester, 2010).

    Book  Google Scholar 

  3. G.-J. Zhao and K.-L. Han (2012). Acc. Chem. Res. 45, 404.

    Article  CAS  Google Scholar 

  4. M.-X. Zhang and G.-J. Zhao (2012). ChemSusChem 5, 879.

    Article  CAS  Google Scholar 

  5. E. Pines, D. Pines, Y.-Z. Ma, and G. R. Fleming (2004). ChemPhysChem 5, 1315.

    Article  CAS  Google Scholar 

  6. G.-J. Zhao and K.-L. Han (2008). Biophys. J. 94, 38.

    Article  CAS  Google Scholar 

  7. S. M. Borisov and O. S. Wolfbeis (2008). Chem. Rev. 108, 423.

    Article  CAS  Google Scholar 

  8. F.-B. Yu, P. Li, G.-Y. Li, G.-J. Zhao, T.-S. Chu, and K.-L. Han (2011). J. Am. Chem. Soc. 133, 11030.

    Article  CAS  Google Scholar 

  9. M. J. Kamlet and R. W. Taft (1976). J. Am. Chem. Soc. 98, 377.

    Article  CAS  Google Scholar 

  10. M. Maroncelli and G. R. Fleming (1987). J. Chem. Phys. 86, 6221.

    Article  CAS  Google Scholar 

  11. J. Kim, U. W. Schmit, J. A. Gruetzmaher, G. A. Voth, and N. E. Scherer (2002). J. Chem. Phys. 116, 737.

    Article  CAS  Google Scholar 

  12. W. P. de Boeij, M. S. Pshenichnikov, and D. A. Wiersma (1998). Annu. Rev. Phys. Chem. 49, 99.

    Article  Google Scholar 

  13. G.-J. Zhao, B. H. Northrop, K.-L. Han, and P. J. Stang (2010). J. Phys. Chem. A 114, 9007.

    Article  CAS  Google Scholar 

  14. G.-J. Zhao and K.-L. Han (2007). J. Chem. Phys. 127, 024306.

    Article  Google Scholar 

  15. N. Mataga, H. Chosrowjan, and S. Taniguchi (2005). J. Photochem. Photobiol. C 6, 37.

    Article  CAS  Google Scholar 

  16. G.-J. Zhao, K.-L. Han, and P. J. Stang (2009). J. Chem. Theory Comput. 5, 1955.

    Article  CAS  Google Scholar 

  17. G.-J. Zhao and K.-L. Han (2008). ChemPhysChem 9, 1842.

    Article  CAS  Google Scholar 

  18. D. Laage and J. T. Hynes (2007). Proc. Natl. Acad. Sci. USA 104, 11167.

    Article  CAS  Google Scholar 

  19. G.-J. Zhao and K.-L. Han (2008). J. Comput. Chem. 29, 2010.

    Article  CAS  Google Scholar 

  20. G. J. Zhao and K. L. Han (2007). J. Phys. Chem. A 111, 9218.

    Article  CAS  Google Scholar 

  21. Y.-H. Liu, G.-J. Zhao, G.-Y. Li, and K.-L. Han (2010). J. Photochem. Photobiol. A 209, 181.

    Article  CAS  Google Scholar 

  22. G.-J. Zhao and K.-L. Han (2009). J. Phys. Chem. A 113, 14329.

    Article  CAS  Google Scholar 

  23. G.-J. Zhao, J.-Y. Liu, L.-C. Zhou, and K.-L. Han (2007). J. Phys. Chem. B 111, 8940.

    Article  CAS  Google Scholar 

  24. N.-N. Wei, C. Hao, Z.-L. Xiu, J.-W. Chen, and J.-S. Qiu (2010). J. Comput. Chem. 31, 2853.

    CAS  Google Scholar 

  25. Y.-F. Liu, C.-F. Zhang, Y.-G. Yang, D.-P. Yang, D.-H. Shi, and J.-F. Sun (2012). J. Clust. Sci. 23, 1029.

    Article  CAS  Google Scholar 

  26. R. Wang, C. Hao, P. Li, N.-N. Wei, J.-W. Chen, and J.-S. Qiu (2010). J. Comput. Chem. 31, 2157.

    Article  CAS  Google Scholar 

  27. G.-J. Zhao and K.-L. Han (2007). J. Phys. Chem. A 111, 2469.

    Article  CAS  Google Scholar 

  28. E. Krystkowiak, K. Dobek, and A. Maciejewski (2006). J. Photochem. Photobiol. A 184, 250.

    Article  CAS  Google Scholar 

  29. A. Maciejewski, E. Krystkowiak, J. Koput, and K. Dobek (2011). ChemPhysChem 12, 322.

    Article  CAS  Google Scholar 

  30. R. J. Cave, K. Burke, and E. W. Castner Jr. (2002). J. Phys. Chem. A 106, 9294.

    Article  CAS  Google Scholar 

  31. D. Jacquemin, E. A. Perpete, X. Assfeld, G. Scalmani, M. J. Frisch, and C. Adamo (2007). Chem. Phys. Lett. 438, 208.

    Article  CAS  Google Scholar 

  32. R. Improta, V. Barone, G. Scanlmaini, and M. J. Frisch (2006). J. Chem. Phys. 125, 054103.

    Article  Google Scholar 

  33. R. Improta, G. Scalmani, M. J. Frisch, and V. Barone (2007). J. Chem. Phys. 127, 074504.

    Article  Google Scholar 

  34. W.-W. Zhao, Y.-H. Ding, and Q.-Y. Xia (2011). J. Comput. Chem. 32, 545.

    Article  CAS  Google Scholar 

  35. S. I. Gorelsky, SWizard Program (University of Ottawa, Ottawa, 2012). http://www.sg-chem.net/.

  36. S. I. Gorelsky and A. B. P. Lever (2001). J. Organomet. Chem. 635, 187.

    Article  CAS  Google Scholar 

  37. D. Jacquemin, E. Perpete, I. Ciofini, and C. Adamo (2009). Acc. Chem. Res. 42, 326.

    Article  CAS  Google Scholar 

  38. J. Tomasi, B. Mennucci, and R. Cammi (2005). Chem. Rev. 105, 2999.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  40. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hrat-chian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dan-nenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowskiand, and D. J. Fox Gaussian 09, Revision A02 (Gaussian Inc., Wallingford, 2009).

    Google Scholar 

  41. P. A. Hunt, B. Kirchner, and T. Welton (2006). Chem. Eur. J. 12, 6762.

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the Innovation Scientists and Technicians Troop Construction Projects of Henan Province of China (Grant No. 124200510013) and the National Natural Science Foundation of China (Grant No. 11274096).

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Authors and Affiliations

  1. Physics Laboratory, North China University of Water Resources and Electric Power, Zhengzhou, 450046, People’s Republic of China

    Dapeng Yang

  2. Department of Electronic Engineering, Henan Economy and Trade Vocational College, Zhengzhou, 450018, People’s Republic of China

    Xiang Li

  3. Department of Physics, Henan Normal University, Xinxiang, 453007, People’s Republic of China

    Yufang Liu

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  1. Dapeng Yang
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  2. Xiang Li
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  3. Yufang Liu
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Correspondence to Dapeng Yang or Yufang Liu.

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Yang, D., Li, X. & Liu, Y. Influence of Hydrogen Bonding and Polarity on the Spectral Properties of 4-Aminophthalimide Clusters Formed with Triethylamine and Dimethyl Sulfoxide in Solution. J Clust Sci 24, 497–513 (2013). https://doi.org/10.1007/s10876-013-0549-4

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