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Synthesis of push–pull porphyrin with two electron-donating and two electron-withdrawing groups and its application to dye-sensitized solar cell

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan

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Yamato Fujimori

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan

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Kenichi Sugiura

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan

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Yukihiro Tsuji

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan

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Seigo Ito

Department of Electrical Engineering and Computer Sciences, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan

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, and

Hiroshi Imahori

Department of Molecular Engineering, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan

Institute for Integrated Cell-Material Sciences (WPI-iCeMS), Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan

Corresponding author.

SPP full member in good standing.

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https://doi.org/10.1142/S1088424614500989Cited by:14 (Source: Crossref)

Abstract

We synthesized for the first time a push–pull porphyrin dye bearing two diarylamino groups and two carboxyphenylethynyl groups as electron-donating and electron-withdrawing anchoring groups, respectively. The absorption spectrum displayed broad and red-shifted absorption, achieving panchromic light-harvesting in visible and NIR regions. Introduction of multiple push–pull groups into meso-positions is a promising strategy for the rational design of porphyrin sensitizers for light-harvesting applications. The preliminary photovoltaic performance is moderate (3.0%), but the extensive photocurrent generation matches with the excellent light-harvesting ability. Further modulation of the photovoltaic properties of porphyrin DSSCs will be possible by suitable selection of electron-donating and electron-withdrawing groups as well as introduction of the substituents into the porphyrin core.

Dedicated to Professor Shunichi Fukuzumi on the occasion of his retirement.

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References

B. O'Regan and M. Grätzel , Nature 353 , 737 ( 1991 ) . Crossref, Web of Science, Google Scholar
M. K. Nazeeruddin et al. , J. Am. Chem. Soc. 127 , 16835 ( 2005 ) . Crossref, Web of Science, Google Scholar
F. Gao et al. , J. Am. Chem. Soc. 130 , 10720 ( 2008 ) . Crossref, Web of Science, Google Scholar
C. Chen et al. , ACS Nano 3 , 3103 ( 2009 ) . Crossref, Web of Science, Google Scholar
L. Han et al. , Energy Environ. Sci. 5 , 6057 ( 2012 ) . Crossref, Web of Science, Google Scholar
A. Mishra , M. K. R. Fischer and P. Bäuerle , Angew. Chem. Int. Ed. 48 , 2474 ( 2009 ) . Crossref, Web of Science, Google Scholar
Y. Ooyama and Y. Harima , Eur. J. Org. Chem. 2903 ( 2009 ) . Crossref, Web of Science, Google Scholar
W. Zeng et al. , Chem. Mater. 22 , 1915 ( 2010 ) . Crossref, Web of Science, Google Scholar
L. L. Tan et al. , J. Mater. Chem. A 2 , 8988 ( 2014 ) . Crossref, Google Scholar
W. M. Campbell et al. , Coord. Chem. Rev. 248 , 1363 ( 2004 ) . Crossref, Web of Science, Google Scholar
H. Imahori , T. Umeyama and S. Ito , Acc. Chem. Res. 42 , 1809 ( 2009 ) . Crossref, Web of Science, Google Scholar
M. V. Martínez-Díaz , G. de la Torre and T. Torres , Chem. Commun. 46 , 7090 ( 2010 ) . Crossref, Web of Science, Google Scholar
L. L. Li and E. W. G. Diau , Chem. Soc. Rev. 42 , 291 ( 2013 ) . Crossref, Web of Science, Google Scholar
K. Ladomenou et al. , RSC Adv. 4 , 21379 ( 2014 ) . Crossref, Web of Science, Google Scholar
H. P. Lu et al. , J. Phys. Chem. C 113 , 20990 ( 2009 ) . Crossref, Web of Science, Google Scholar
T. Bessho et al. , Angew. Chem. Int. Ed. 49 , 6646 ( 2010 ) . Crossref, Web of Science, Google Scholar
A. Yella et al. , Science 334 , 629 ( 2011 ) . Crossref, Web of Science, Google Scholar
K. Kurotobi et al. , Chem. Eur. J. 19 , 17075 ( 2013 ) . Crossref, Web of Science, Google Scholar
A. Yella et al. , Angew. Chem. Int. Ed. 53 , 2973 ( 2014 ) . Crossref, Web of Science, Google Scholar
S. Mathew et al. , Nature Chem. 6 , 242 ( 2014 ) . Crossref, Web of Science, Google Scholar
J. Luo et al. , J. Am. Chem. Soc. 136 , 265 ( 2014 ) . Crossref, Web of Science, Google Scholar
H. Imahori et al. , J. Phys. Chem. C 114 , 10656 ( 2010 ) . Crossref, Web of Science, Google Scholar
S. Taniguchi et al. , Tetrahedron 57 , 2103 ( 2001 ) . Crossref, Web of Science, Google Scholar
O. Robles and F. E. McDonald , Org. Lett. 10 , 1811 ( 2008 ) . Crossref, Web of Science, Google Scholar
D. M. Shen et al. , J. Org. Chem. 74 , 206 ( 2009 ) . Crossref, Web of Science, Google Scholar
Frisch MJ et al. Gaussian 09, revision C.01, Gaussian, Inc., Wallingford, CT, 2010 . Google Scholar
X. Xue et al. , RSC Adv. 4 , 8894 ( 2014 ) . Crossref, Web of Science, Google Scholar
H. Imahori et al. , J. Phys. Chem. A 115 , 3679 ( 2011 ) . Crossref, Web of Science, Google Scholar
S. Ye et al. , J. Phys. Chem. C 117 , 6066 ( 2013 ) . Crossref, Web of Science, Google Scholar
H. Hayashi et al. , ChemSusChem 6 , 508 ( 2013 ) . Crossref, Web of Science, Google Scholar
S. Ito et al. , Thin Solid Films 516 , 4613 ( 2008 ) . Crossref, Web of Science, Google Scholar