Issue
Copyright (c) 2014 Chun Ming Jiao, Bing Jun Li, Si Li Yi, Qing Xu*
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis and Photoelectric Properties of Donor-Acceptor-Donor Molecule Containing Perylene Diimide
Corresponding Author(s) : Chun Ming Jiao
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
In this paper, a novel perylene diimide derivative 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide (PDI-TPA) was synthesized and characterized by IR spectroscopy, 1H NMR and elemental analysis. Besides, solubility and photoelectric properties of 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide were studied. Results show that 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide exhibits excellent solubility in common solvents. The absorption bands span a wide range of the visible spectra and optical band gap is 1.68 eV. In addition, 1,7-bis[N,N-bis(4-phenyl)aniline]perylene diimide exhibits an ambipolar behaviour, the highest occupied molecular orbital (HOMO) energy level and the lowest unoccupied molecular orbital (LUMO) energy level are -5.64 eV and -3.94 eV, respectively.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- Z. Sen, Pror. Energy Combust. Sci., 30, 367 (2004).
- W.Y. Zhou, Y.G. Wen, L.C. Ma, Y.Q. Liu and X.W. Zhan, Macromole-cules, 45, 4115 (2012).
- R.M. Williams, N. Vân Anh and I.H.M. van Stokkum, J. Phys. Chem. B, 117, 11239 (2013).
- H. Langhals, O. Krotz, K. Polborn and P. Mayer, Angew. Chem. Int. Ed., 44, 2427 (2005).
- Y. Shibano, T. Umeyama, Y. Matano, N.V. Tkachenko, H. Lemmetyinen, Y. Araki, O. Ito and H. Imahori, J. Phys. Chem. C, 111, 6133 (2007).
- T.W. Holcombe, J.E. Norton, J. Rivnay, C.H. Woo, L. Goris, C. Piliego, G. Griffini, A. Sellinger, J.-L. Bredas, A. Salleo and J.M.J. Frechet, J. Am. Chem. Soc., 133, 12106 (2011).
- E.J. Zhou, J.Z. Cong, Q.S. Wei, K. Tajima, C.H. Yang and K. Hashimoto, Angew. Chem. Int. Ed., 50, 2799 (2011).
- T.M. Wilson, M.J. Tauber and M.R. Wasielewski, J. Am. Chem. Soc., 131, 8952 (2009).
- S.H. Oh, B.G. Kim, S.J. Yun, M. Maheswara, K. Kim and J.Y. Do, Dyes Pigments, 85, 37 (2010).
- C.B. Fan, S.Z. Pu, G. Liu and T.S. Yang, J. Photochem. Photobiol. A, 194, 333 (2008).
- H.W. Chang, K.H. Lin, C.C. Chueh, G.S. Liou and W.C. Chen, J. Polym. Sci. A Polym. Chem., 47, 4037 (2009).
- Y.D. Zhang, H.L. Wang, Y. Xiao, L.G. Wang, D.Q. Shi and C.H. Cheng, Appl. Mater. Interfaces, 5, 11093 (2013).
- G.S. Liou, Y.L. Yang, W.C. Chen and Y.O. Su, J. Polym. Sci. A Polym. Chem., 45, 3292 (2007).
- K. Yuan Chiu, T. Xiang Su, J. Hong Li, T.-H. Lin, G.-S. Liou and S.-H. Cheng, J. Electroanal. Chem., 575, 95 (2005).
- F. Würthner, V. Stepanenko, Z. Chen, C.R. Saha-Möller, N. Kocher and D. Stalke, Org. Chem., 69, 7933 (2004).
- E.M. Calzado, J.M. Villalvilla, P.G. Boj, J.A. Quintana, R. Gomez, J.L. Segura and M.A. Diaz-Garcia, J. Phys. Chem. C, 111, 13595 (2007).
- C.C. Chao, M.K. Leung, Y.O. Su, K.Y. Chiu, T.H. Lin, S.J. Shieh and S.C. Lin, J. Org. Chem., 70, 4323 (2005).
- S. Vajiravelu, L. Ramunas, G. Juozas Vidas, G. Valentas, J. Vygintas and S. Valiyaveettil, J. Mater. Chem., 19, 4268 (2009).
- M. Antonietta Loi, P. Denk, H. Hoppe, H. Neugebauer, C. Winder, D. Meissner, C. Brabec, N. Serdar Sariciftci, A. Gouloumis, P. Vázquez and T. Torres, J. Mater. Chem., 13, 700 (2003).
- R. Gómez, J.L. Segura and N. Martín, Org. Lett., 7, 717 (2005).
- J.L. Segura, R. Gómez, R. Blanco, E. Reinold and P. Bäuerle, Chem. Mater., 18, 2834 (2006).
- A.R. Rabindranath, Y. Zhu, I. Heim and B. Tieke, Macromolecules, 39, 8250 (2006).
- M. Luo, H. Shadnia, G. Qian, X.B. Du, D.B. Yu, D.G. Ma, J.S. Wright and Z.Y. Wang, Chem. Eur. J., 15, 8902 (2009).
References
Z. Sen, Pror. Energy Combust. Sci., 30, 367 (2004).
W.Y. Zhou, Y.G. Wen, L.C. Ma, Y.Q. Liu and X.W. Zhan, Macromole-cules, 45, 4115 (2012).
R.M. Williams, N. Vân Anh and I.H.M. van Stokkum, J. Phys. Chem. B, 117, 11239 (2013).
H. Langhals, O. Krotz, K. Polborn and P. Mayer, Angew. Chem. Int. Ed., 44, 2427 (2005).
Y. Shibano, T. Umeyama, Y. Matano, N.V. Tkachenko, H. Lemmetyinen, Y. Araki, O. Ito and H. Imahori, J. Phys. Chem. C, 111, 6133 (2007).
T.W. Holcombe, J.E. Norton, J. Rivnay, C.H. Woo, L. Goris, C. Piliego, G. Griffini, A. Sellinger, J.-L. Bredas, A. Salleo and J.M.J. Frechet, J. Am. Chem. Soc., 133, 12106 (2011).
E.J. Zhou, J.Z. Cong, Q.S. Wei, K. Tajima, C.H. Yang and K. Hashimoto, Angew. Chem. Int. Ed., 50, 2799 (2011).
T.M. Wilson, M.J. Tauber and M.R. Wasielewski, J. Am. Chem. Soc., 131, 8952 (2009).
S.H. Oh, B.G. Kim, S.J. Yun, M. Maheswara, K. Kim and J.Y. Do, Dyes Pigments, 85, 37 (2010).
C.B. Fan, S.Z. Pu, G. Liu and T.S. Yang, J. Photochem. Photobiol. A, 194, 333 (2008).
H.W. Chang, K.H. Lin, C.C. Chueh, G.S. Liou and W.C. Chen, J. Polym. Sci. A Polym. Chem., 47, 4037 (2009).
Y.D. Zhang, H.L. Wang, Y. Xiao, L.G. Wang, D.Q. Shi and C.H. Cheng, Appl. Mater. Interfaces, 5, 11093 (2013).
G.S. Liou, Y.L. Yang, W.C. Chen and Y.O. Su, J. Polym. Sci. A Polym. Chem., 45, 3292 (2007).
K. Yuan Chiu, T. Xiang Su, J. Hong Li, T.-H. Lin, G.-S. Liou and S.-H. Cheng, J. Electroanal. Chem., 575, 95 (2005).
F. Würthner, V. Stepanenko, Z. Chen, C.R. Saha-Möller, N. Kocher and D. Stalke, Org. Chem., 69, 7933 (2004).
E.M. Calzado, J.M. Villalvilla, P.G. Boj, J.A. Quintana, R. Gomez, J.L. Segura and M.A. Diaz-Garcia, J. Phys. Chem. C, 111, 13595 (2007).
C.C. Chao, M.K. Leung, Y.O. Su, K.Y. Chiu, T.H. Lin, S.J. Shieh and S.C. Lin, J. Org. Chem., 70, 4323 (2005).
S. Vajiravelu, L. Ramunas, G. Juozas Vidas, G. Valentas, J. Vygintas and S. Valiyaveettil, J. Mater. Chem., 19, 4268 (2009).
M. Antonietta Loi, P. Denk, H. Hoppe, H. Neugebauer, C. Winder, D. Meissner, C. Brabec, N. Serdar Sariciftci, A. Gouloumis, P. Vázquez and T. Torres, J. Mater. Chem., 13, 700 (2003).
R. Gómez, J.L. Segura and N. Martín, Org. Lett., 7, 717 (2005).
J.L. Segura, R. Gómez, R. Blanco, E. Reinold and P. Bäuerle, Chem. Mater., 18, 2834 (2006).
A.R. Rabindranath, Y. Zhu, I. Heim and B. Tieke, Macromolecules, 39, 8250 (2006).
M. Luo, H. Shadnia, G. Qian, X.B. Du, D.B. Yu, D.G. Ma, J.S. Wright and Z.Y. Wang, Chem. Eur. J., 15, 8902 (2009).