ArticlesNo Access

Diporphyrin magnesium complex with long-wavelength light absorption for organic solar cells

Takenari Sato

Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Search for more papers by this author

Takafumi Nakagawa

Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Search for more papers by this author

Hiroshi Okada

Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Search for more papers by this author

, and

Yutaka Matsuo

Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Corresponding author, tel/fax: +81 3-5841-1476.

SPP full member in good standing.

Search for more papers by this author

https://doi.org/10.1142/S1088424615500303Cited by:6 (Source: Crossref)

Abstract

We synthesized a diporphyrin compound [4,7-bis[5-[arylethynyl]-10,20-bis{(triisopropylsilyl)ethynyl}porphyrin-15-yl]]-2,1,3-benzothiadiazole dimagnesium(II)], in which two porphyrin units were linked using a benzodiathiazole unit as an electron-withdrawing moiety. These diporphyrins have low-lying HOMO and LUMO levels with long-wavelength light absorption property. Power conversion efficiency of the organic solar cell using this diporphyrin and mix-PCBM (a 85:15 mixture of [6,6]-phenyl-C₆₁-butyric acid methyl ester (PC₆₁BM) and [6,6]-phenyl-C₇₁-butyric acid methyl ester (PC₇₁BM) was 2.75% with short-circuit current density of 8.79 mA/cm², open-circuit voltage of 0.80 V, and fill factor of 0.39. Photocurrent conversion in the near infrared region was demonstrated by the incident photon-to-current efficiency spectrum.

Dedicated to Professor Shunichi Fukuzumi on the occasion of his retirement

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

(a) Martínez-Díaz MV, Torre G and Torres T. Chem. Commun. 2010; 46: 7090–7108. (b) Imahori H, Umeyama T, Kurotobi K and Takano Y. Chem. Commun. 2012; 48: 4032–4045. (c) Luo J, Xu M, Li R, Huang K-W, Jiang C, Qi Q, Zeng W, Zhang J, Chi C, Wang P and Wu J. J. Am. Chem. Soc. 2014; 136: 265–272. (d) Kurotobi K, Toude Y, Kawamoto K, Fujimori Y, Ito S, Chabera P, Sundström V and Imahori H. Chem. Eur. J. 2013; 19: 17075–17081. (e) Yella A, Mai C-L, Zakeeruddin SM, Chang S-N, Hsieh C-H, Yeh C-Y and Gräzel M. Angew. Chem. 2014; 126: 3017–3021. (f) Mathew S, Yella A, Gao P, Humphry-Baker R, Curchod BFE, Ashari-Astani N, Tavernelli I, Rothlisberger U, Nazeeruddin MK and Gräzel M. Nature Chem. 2014; 6: 242–247 . Google Scholar
For example; (a) Yella A, Lee H-W, Tsao HN, Yi C, Chandiran AK, Nazeeruddin MK, Diau EW-G, Yeh C-Y, Zakeeruddin SM and Grätzel M. Science 2011; 334: 629–634. (b) Khan SM, Kaur M, Heflin JR and Sayyad MHJ. Phys. Chem. Solids. 2011; 72: 1430–1435 (c) Li L-L and Diau EW-G Chem. Soc. Rev. 2013; 42: 291–304. (d) Lu J, Zhang B, Yuan H, Xu X, Cao K, Cui J, Liu S, Shen Y, Cheng Y, Xu J and Wang M. J. Phys. Chem. C 2014; 118: 14739–14748 . Google Scholar
(a) Waltera MG, Rudineb AB and Wamser CC. J. Porphyrins Phthalocyanines 2010; 14: 759–792. (b) Li L, Huang Y, Peng J, Cao Y and Peng X. J. Mater. Chem. A 2013; 1: 2144–2150. (c) Qin H, Li L, Guo F, Su S, Peng J, Cao Y and Peng X. Energy Environ. Sci. 2014; 7: 1397–1401 . Google Scholar
(a) Hatano J, Obata N, Yamaguchi S, Yasuda T and Matsuo Y. J. Mater. Chem. 2012; 22: 19258–19263. (b) Yamamoto T, Hatano J, Nakagawa T, Yamaguchi S and Matsuo Y. Appl. Phys. Lett. 2013; 102: 013305. (c) Matsuo Y, Hatano J and Nakagawa T. J. Phys. Org. Chem. 2014; 27: 87–93. (d) Nakagawa T, Hatano J and Matsuo Y. J. Porphyrins Phthalocyanines 2014; 18: 735–740 . Google Scholar
(a) Borovkov V. Symmetry 2014; 6: 256–294. (b) Anyika M, Gholami H, Ashtekar KD, Acho R and Borhan B. J. Am. Chem. Soc. 2014; 136: 550–553 . Google Scholar
(a) Susumu K, Duncan TV and Therien MJ. J. Am. Chem. Soc. 2005; 127: 5186–5195. (b) Balaz M, Collins HA, Dahlstedt E and Anderson HL. Org. Biomol. Chem. 2009; 7: 874–888. (c) Fisher JAN, Susumu K, Therien MJ and Yodh AG. J. Chem. Phys. 2009; 130: 134506. (d) Mai C-L, Huang W-K, Lu H-P, Lee C-W, Chiu C-L, Liang Y-R, Diau EW-G and Yeh C-Y. Chem. Commun. 2010; 46: 809–811 . Google Scholar
B. Walker , C. Kim and T.-Q. Nguyen , Chem. Mater 23 , 470 ( 2011 ) . Crossref, Web of Science, Google Scholar
(a) Taylor PN, Wylie AP, Huuskonen J and Anderson HL. Angew. Chem. Int. Ed. 1998; 37: 986–989 (b) Davis NKS, Thompson AL and Anderson HL. J. Am. Chem. Soc. 2011; 133: 30–31. (c) Yella A, Mai C-L, Zakeeruddin SM, Chang S-N, Hsieh C-H, Yeh C-Y and Grätzel M. Angew Chem. Int. Ed. 2014; 126: 3017–3021. (d) Wang C-L, Hu J-Y, Wu C-H, Kuo H-H, Chang Y-C, Lan Z-J, Wu H-P, Diau EW-G and Lin C-Y. Energy Environ. Sci. 2014; 7: 1392–1396 . Google Scholar
Y. J. Cheng , S. H. Yang and C. S. Hsu , Chem. Rev. 109 , 5868 ( 2009 ) . Crossref, Web of Science, Google Scholar
T. E. O. Screen et al. , J. Mater. Chem 11 , 312 ( 2001 ) . Crossref, Web of Science, Google Scholar
X. Huang et al. , Polym. Sci. Part A; Polym. Chem 48 , 997 ( 2010 ) . Crossref, Web of Science, Google Scholar