Synthesis and Characterization of Triphenylamine Appended Porphyrins and their Intramolecular Energy Transfer

M. Bai; Q. Ma; R. Song; F. Meng

doi:10.14233/ajchem.2014.15648

Issue

Vol. 26 No. 7 (2014): Vol 26 Issue 7

Issue Published : March 22, 2014

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Characterization of Triphenylamine Appended Porphyrins and their Intramolecular Energy Transfer

https://doi.org/10.14233/ajchem.2014.15648

M. Bai

Marine College, Shandong University, Weihai 264209, P.R. China

Q. Ma

Marine College, Shandong University, Weihai 264209, P.R. China

R. Song

Marine College, Shandong University, Weihai 264209, P.R. China

F. Meng

Marine College, Shandong University, Weihai 264209, P.R. China

Corresponding Author(s) : M. Bai

ming_bai@sdu.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 7 (2014): Vol 26 Issue 7
Article Published : March 31, 2014

Abstract

A series of 5,10,15-triphenyl-20-(triphenylamino)porphyrinato zinc(II) (ZnTPP(TPA)₁ (1), 5-phenyl-10,15,20-tris(triphenylamino)-porphyrinato zinc(II) (ZnTPP(TPA)₃ (2) and 5,10,15,20-tris(triphenylamino)porphyrinato zinc(II) (ZnTPP(TPA)₄ (3) were synthesized using 4-(N,N-diphenylamino)benzaldehyde, benzaldehyde and pyrrole as starting materials. All porphyrins were characterized with various spectroscopic methods, MALDI-TOF mass, UV-vis, ¹H NMR and 2D COSY spectroscopy. The structure of 5,10,15-triphenyl-20-(triphenylamino)porphyrin [H₂TPP(TPA)] was also established by X-ray diffraction analyses. The absorption and emission spectra indicate that there are strong interactions between zinc porphyrin core and triarylamine at ground states. Excited energy transfer from triphenylamine to porphyrin was proved by the fluorescence spectra.

Keywords

Triphenylamine Porphyrin Energy transfer

Bai, M., Ma, Q., Song, R., & Meng, F. (2014). Synthesis and Characterization of Triphenylamine Appended Porphyrins and their Intramolecular Energy Transfer. Asian Journal of Chemistry, 26(7), 2053–2056. https://doi.org/10.14233/ajchem.2014.15648

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References

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Crystal data C57H40Cl3N5, M = 901.29, monoclinic, P2/c, Z = 4, a = 10.3366(3) Å, b = 22.2075(6) Å, c = 20.2667(5) Å, α = 90°, β = 91.983(2)°, γ = 90°, U = 4649.4(2) Å3, Dcalc = 1.288 g.cm-3, 15,870 independent data were collected with graphite monochromatic Cu Kα radiation (λ = 1.54178 Å) using the SMART and SAINT programs at 293(2) K using Oxford Diffraction Gemini E diffractometer. The structures were solved by the direct method (SHELXS-97). Anisotropic thermal parameters were used for the non-hydrogen atoms and isotropic parameters for the hydrogen atoms. Hydrogen atoms were added geometrically and refined using a riding model. The structure was refined by full-matrix least-squares (SHELXS-97) on F2 to R1 = 0.0537, wR2 = 0.1582 for 7880 reflections with I > 2σ(I) respectively. CCDC 723302 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam. ac.uk/data_request/cif.

References

K.M. Kadish, in eds.: K.M. Kadish, K.M. Smith and R. Guilard, The Porphyrin Handbook, Academic Press, San Diego, CA, vol. 1, pp. 1-44 (2000).

K.M. Kadish, E.V. Caemelbecke and G. Royal, in eds.: K.M. Kadish, K.M. Smith and R. Guilard, The Porphyrin Handbook, Academic Press, San Diego, CA, vol. 8, pp. 3-114 (2000).

A. Iwan and D. Sek, Prog. Polym. Sci., 36, 1277 (2011); doi:10.1016/j.progpolymsci.2011.05.001.

Y. Tao, C. Yang and J. Qin, Chem. Soc. Rev., 40, 2943 (2011); doi:10.1039/c0cs00160k.

A. Chaskar, H.-F. Chen and K.-T. Wong, Adv. Mater., 23, 3876 (2011); doi:10.1002/adma.201101848.

J. He, F. Guo, X. Li, W. Wu, J. Yang and J. Hua, Chem. Eur. J., 18, 7903 (2012); doi:10.1002/chem.201103702.

K. Pei, Y. Wu, W. Wu, Q. Zhang, B. Chen, H. Tian and W. Zhu, Chem. Eur. J., 18, 8190 (2012); doi:10.1002/chem.201103542.

D.W. Chang, H.J. Lee, J.H. Kim, S.Y. Park, S.-M. Park, L. Dai and J.-B. Baek, Org. Lett., 13, 3880 (2011); doi:10.1021/ol2012378.

Y. Ooyama and Y. Harima, Eur. J. Org. Chem., 2009, 2903 (2009); doi:10.1002/ejoc.200900236.

H.-J. Yen and G.-S. Liou, Polym. Chem., 3, 255 (2012); doi:10.1039/c1py00346a.

C.-P. Hsieh, H.-P. Lu, C.-L. Chiu, C.-W. Lee, S.-H. Chuang, C.-L. Mai, W.-N. Yen, S.-J. Hsu, E.W.-G. Diau and C.-Y. Yeh, J. Mater. Chem., 20, 1127 (2010); doi:10.1039/b919645e.

B. Liu, W. Zhu, Y. Wang, W. Wu, X. Li, B. Chen, Y.-T. Long and Y. Xie, J. Mater. Chem., 22, 7434 (2012); doi:10.1039/c2jm16804a.

M. Zhu, Y. Dong, Y. Du, Z. Mou, J. Liu, P. Yang and X. Wang, Chem. Eur. J., 18, 4367 (2012); doi:10.1002/chem.201102595.

K. Noworyta, W. Kutner, C.A. Wijesinghe, S.G. Srour and F. D'Souza, Anal. Chem., 84, 2154 (2012); doi:10.1021/ac2021344.

C.-Y. Huang and Y.O. Su, Dalton Trans., 39, 8306 (2010); doi:10.1039/c0dt00199f.

C.-Y. Huang, C.-Y. Hsu, L.-Y. Yang, C.-J. Lee, T.-F. Yang, C.-C. Hsu, C.-H. Ke and Y.O. Su, Eur. J. Inorg. Chem., 1038 (2012); doi:10.1002/ejic.201101033.

Crystal data C57H40Cl3N5, M = 901.29, monoclinic, P2/c, Z = 4, a = 10.3366(3) Å, b = 22.2075(6) Å, c = 20.2667(5) Å, α = 90°, β = 91.983(2)°, γ = 90°, U = 4649.4(2) Å3, Dcalc = 1.288 g.cm-3, 15,870 independent data were collected with graphite monochromatic Cu Kα radiation (λ = 1.54178 Å) using the SMART and SAINT programs at 293(2) K using Oxford Diffraction Gemini E diffractometer. The structures were solved by the direct method (SHELXS-97). Anisotropic thermal parameters were used for the non-hydrogen atoms and isotropic parameters for the hydrogen atoms. Hydrogen atoms were added geometrically and refined using a riding model. The structure was refined by full-matrix least-squares (SHELXS-97) on F2 to R1 = 0.0537, wR2 = 0.1582 for 7880 reflections with I > 2σ(I) respectively. CCDC 723302 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam. ac.uk/data_request/cif.

Issue

Vol. 26 No. 7 (2014): Vol 26 Issue 7

Synthesis and Characterization of Triphenylamine Appended Porphyrins and their Intramolecular Energy Transfer

Corresponding Author(s) : M. Bai

Abstract

Keywords

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