Synthesis and Optical/Electrochemical Properties of meso-5,10,15,20-Tetrathienyl Substituted Porphyrins and Their Metal Complexes

Yong Zhou; Fude Liu; Haiyan Wu; Boyang Qu; Lijie Duan

doi:10.14233/ajchem.2015.17089

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Issue Published : January 10, 2015

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

Synthesis and Optical/Electrochemical Properties of meso-5,10,15,20-Tetrathienyl Substituted Porphyrins and Their Metal Complexes

https://doi.org/10.14233/ajchem.2015.17089

Yong Zhou

Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P.R. China

Fude Liu

Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P.R. China

Haiyan Wu

Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P.R. China

Boyang Qu

Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P.R. China

Lijie Duan

Tianjin Key Laboratory of Organic Solar Cells and Photochemical Conversion, School of Chemistry & Chemical Engineering, Tianjin University of Technology, Tianjin 300384, P.R. China

Corresponding Author(s) : Fude Liu

liufude@tjut.edu.cn; 15202206925@126.com

Asian Journal of Chemistry, Vol. 27 No. 2 (2015): Vol 27 Issue 2
Article Published : January 10, 2015

Abstract

Two kinds of meso-5,10,15,20-tetrathienyl substituted porphyrin compounds, meso-5,10,15,20-tetra(2-thienyl)porphyrin (H₂TTP), meso-5,10,15,20-tetra(3-methyl-2-thienyl)porphyrin [H₂T(3-M)TP] and their metal complexes were synthesized and characterized by IR, ¹H NMR. UV-visible absorption spectra, fluorescence spectra, photoluminescence spectra and the cyclic voltammograms of the synthesized porphyrins and metalloporphyrins. Optical properties reveal that zinc porphyrin possesses intensive fluorescence emission, whereas cobalt(II) and copper(II) porphyrins exhibit no fluorescence emission. When the complexation of H₂TTP and H₂T(3-M)TP with metal ions occur, the electrochemical band-gaps (Eg) increase meanwhile the E_LUMO shows smaller change than that of the E_HOMO. The values of ionization potential, electronic affinity, HOMO energy level (E_HOMO) and LUMO energy level (E_LUMO) of the synthesized porphyrins and metalloporphyrins were also given in the paper.

Keywords

Porphyrin Metalloporphyrin Electrochemical properties Optical properties Zn(II) Co(II) Cu(II)

Zhou, Y., Liu, F., Wu, H., Qu, B., & Duan, L. (2015). Synthesis and Optical/Electrochemical Properties of meso-5,10,15,20-Tetrathienyl Substituted Porphyrins and Their Metal Complexes. Asian Journal of Chemistry, 27(2), 616–620. https://doi.org/10.14233/ajchem.2015.17089

Download Citation

References

X. Zhang, T.T. Steckler, R.R. Dasari, S. Ohira, W.J. Potscavage, S.P. Tiwari, S. Coppée, S. Ellinger, S. Barlow, J.-L. Brédas, B. Kippelen, J.R. Reynolds and S.R. Marder, J. Mater. Chem., 20, 123 (2009); doi:10.1039/b915940a.
M.M. Wienk, M. Turbiez, J. Gilot and R.A.J. Janssen, Adv. Mater., 20, 2556 (2008); doi:10.1002/adma.200800456.
R.F. Service, Science, 332, 293 (2011); doi:10.1126/science.332.6027.293.
E. Bundgaard and F.C. Krebs, Sol. Energy Mater. Sol. Cells, 91, 954 (2007); doi:10.1016/j.solmat.2007.01.015.
A.R. Battersby, Nat. Prod. Rep., 17, 507 (2000); doi:10.1039/b002635m.
M.G. Walter, A.B. Rudine and C.C. Wamser, J. Porphyr. Phthalocyan., 14, 759 (2010); doi:10.1142/S1088424610002689.
G. Calogero, G. Di Marco, S. Caramori, S. Cazzanti, R. Argazzi and C.A. Bignozzi, Energy Environ. Sci., 2, 1162 (2009); doi:10.1039/b913248c.
T.D. Mody, J. Porphyr. Phthalocyan., 4, 362 (2000); doi:10.1002/(SICI)1099-1409(200006/07)4:4<362::AID-JPP250>3.0.CO;2-Z.
Z. Wang, C.J. Medforth and J.A. Shelnutt, J. Am. Chem. Soc., 126, 16720 (2004); doi:10.1021/ja044148k.
Y.J. Cheng, S.H. Yang and C.S. Hsu, Chem. Rev., 109, 5868 (2009); doi:10.1021/cr900182s.
Y. Mao, Z. Fang, Z.H. Zhang and P. Gu, J. Power Sources, 32, 546 (2008).
L.Z. Wang and Y.B. She, Spectrosc. Spectr. Anal., 28, 2312 (2008).
B. Alies, E. Renaglia, M. Rózga, W. Bal, P. Faller and C. Hureau, Anal. Chem., 85, 1501 (2013); doi:10.1021/ac302629u.
K. Ranjith, S.K. Swathi, P. Kumar and P.C. Ramamurthy, Sol. Energy Mater. Sol. Cells, 98, 448 (2012); doi:10.1016/j.solmat.2011.11.034.

References

X. Zhang, T.T. Steckler, R.R. Dasari, S. Ohira, W.J. Potscavage, S.P. Tiwari, S. Coppée, S. Ellinger, S. Barlow, J.-L. Brédas, B. Kippelen, J.R. Reynolds and S.R. Marder, J. Mater. Chem., 20, 123 (2009); doi:10.1039/b915940a.

M.M. Wienk, M. Turbiez, J. Gilot and R.A.J. Janssen, Adv. Mater., 20, 2556 (2008); doi:10.1002/adma.200800456.

R.F. Service, Science, 332, 293 (2011); doi:10.1126/science.332.6027.293.

E. Bundgaard and F.C. Krebs, Sol. Energy Mater. Sol. Cells, 91, 954 (2007); doi:10.1016/j.solmat.2007.01.015.

A.R. Battersby, Nat. Prod. Rep., 17, 507 (2000); doi:10.1039/b002635m.

M.G. Walter, A.B. Rudine and C.C. Wamser, J. Porphyr. Phthalocyan., 14, 759 (2010); doi:10.1142/S1088424610002689.

G. Calogero, G. Di Marco, S. Caramori, S. Cazzanti, R. Argazzi and C.A. Bignozzi, Energy Environ. Sci., 2, 1162 (2009); doi:10.1039/b913248c.

T.D. Mody, J. Porphyr. Phthalocyan., 4, 362 (2000); doi:10.1002/(SICI)1099-1409(200006/07)4:4<362::AID-JPP250>3.0.CO;2-Z.

Z. Wang, C.J. Medforth and J.A. Shelnutt, J. Am. Chem. Soc., 126, 16720 (2004); doi:10.1021/ja044148k.

Y.J. Cheng, S.H. Yang and C.S. Hsu, Chem. Rev., 109, 5868 (2009); doi:10.1021/cr900182s.

Y. Mao, Z. Fang, Z.H. Zhang and P. Gu, J. Power Sources, 32, 546 (2008).

L.Z. Wang and Y.B. She, Spectrosc. Spectr. Anal., 28, 2312 (2008).

B. Alies, E. Renaglia, M. Rózga, W. Bal, P. Faller and C. Hureau, Anal. Chem., 85, 1501 (2013); doi:10.1021/ac302629u.

K. Ranjith, S.K. Swathi, P. Kumar and P.C. Ramamurthy, Sol. Energy Mater. Sol. Cells, 98, 448 (2012); doi:10.1016/j.solmat.2011.11.034.

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Synthesis and Optical/Electrochemical Properties of meso-5,10,15,20-Tetrathienyl Substituted Porphyrins and Their Metal Complexes

Corresponding Author(s) : Fude Liu

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents