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Journal of Materials Science: Materials in Electronics

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30-08-2017

Effect of electron-deficient linkers on the physical and photovoltaic properties of dithienopyrrole-based organic dyes

Authors: Sunil Kumar, K. R. Justin Thomas, Chun-Ting Li, Kuo-Chuan Ho

Published in: Journal of Materials Science: Materials in Electronics | Issue 24/2017

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Abstract

Organic sensitizers containing dithienopyrrole donor, benzotriazole or quinoxaline in the conjugation pathway, and cyanoacrylic acid acceptor featured in a donor–acceptor-π–acceptor configuration are reported. The effect of the nature of different conjugating bridges on photophysical, electrochemical and photovoltaic properties was systematically evaluated. The incorporation auxiliary acceptors broadened the absorption spectra and modulated the excited state energy levels. The DFT calculation unraveled a significant overlap of HOMO and LUMO orbitals in benzotriazole-containing dyes and the charge transfer character for the longer wavelength absorption. Among the dyes, a dye containing benzotriazole and thiophene in the conjugation pathway exhibited highest power conversion efficiency attributable to efficient electron injection and pronounced inhibition of electron recombination.

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B. O’Regan, M. Grätzel, Nature 353, 737–740 (1991)

M. Grätzel, J. Photochem. Photobiol. C 4, 145–153 (2003)

Z. Ning, Y. Fu, H. Tian, Energy. Environ. Sci. 3, 1170–1181 (2010)

C. Grätzel, S.M. Zakeeruddin, Mater. Today 16, 11–18 (2013)

J.-Q. Jiang, C.-L. Sun, Z.-F. Shi, H.-L. Zhang, RSC Adv. 4, 32987–32996 (2014)

C.-P. Lee, R.Y.-Y. Lin, L.-Y. Lin, C.-T. Li, T.-C. Chu, S.-S. Sun, J.T. Lin, K.-C. Ho, RSC Adv. 5, 23810–23825 (2015)

G. Chen, H. Sasabe, T. Igarashi, Z. Hong, J. Kido, J. Mater. Chem. A 3, 14517–1453 (2015)

S. Mathew, A. Yella, P. Gao, R. Humphry-Baker, B.F. Curchod, N. Ashari-Astani, I. Tavernelli, U. Rothlisberger, M.K. Nazeeruddin, M. Grätzel, Nat. Chem. 6, 242–247 (2014)

C.-Y. Chen, M. Wang, J.-Y. Li, N. Pootrakulchote, L. Alibabaei, C.-H. Ngoc-le, J.-D. Decoppet, J.-H. Tsai, C. Grätzel, C.-G. Wu, S.M. Zakeeruddin, M. Grätzel, ACS Nano 3, 3103–3109 (2009)

10.

Z. Yao, M. Zhang, H. Wu, L. Yang, R. Li, P. Wang, J. Am. Chem. Soc. 137, 3799–3808 (2015)

11.

A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, H. Pettersson, Chem. Rev. 110, 6595–6663 (2010)

12.

A. Mishra, M.K.R. Fischer, P. Bäuerle, Angew. Chem. Int. Ed. 48, 2474–2499 (2009)

13.

M. Liang, J. Chen, Chem. Soc. Rev. 42, 3453–3488 (2013)

14.

W.H. Zhu, Y.Z. Wu, S.T. Wang, W.Q. Li, X. Li, J. Chen, Z.S. Wang, H. Tian, Adv. Funct. Mater. 21, 756–763 (2011)

15.

Y. Wu, W. Zhu, Chem. Soc. Rev. 42, 2039–2058 (2013)

16.

Y. Wu, W.-H. Zhu, S.M. Zakeeruddin, M. Grätzel, ACS Appl. Mater. Interfaces 7, 9307–9318 (2015)

17.

Y.Z. Wu, M. Marszalek, S.M. Zakeeruddin, Q. Zhang, H. Tian, M. Grätzel, W.H. Zhu, Energy Environ. Sci. 5, 8261–8272 (2012)

18.

H.B. Zhu, W.Q. Li, Y.Z. Wu, B. Liu, S.Q. Zhu, X. Li, H. Ågren, W.H. Zhu, ACS Sustain. Chem. Eng. 2, 1026–1034 (2014)

19.

Z. Yao, M. Zhang, R. Li, L. Yang, Y. Qiao, P. Wang, Angew. Chem. Int. Ed. 54, 5994–6008 (2015)

20.

J. Mao, F. Guo, W. Ying, W. Wu, J. Li, J. Hua, Chem. Asian J. 7, 982 (2012)

21.

Y. Yen, C. Lee, C. Hsu, H. Chou, Y. Chen, J.T. Lin, Chem. Asian J. 8, 809–816 (2013)

22.

J.-S. Ni, Y.-C. Yen, J.T. Lin, Chem. Commun. 51, 17080–17083 (2015)

23.

J. Yang, P. Ganesan, J. Teuscher, T. Moehl, Y.J. Kim, C. Yi, P. Comte, K. Pei, T.W. Holcombe, M.K. Nazeeruddin, J. Hua, S.M. Zakeeruddin, H. Tian, M. Grätzel, J. Am. Chem. Soc. 136, 5722–5730 (2014)

24.

X. Li, Y. Hu, I. Sanchez-Molina, Y. Zhou, F. Yu, S.A. Haque, W. Wu, J. Hua, H. Tiana, N. Robertson, J. Mater. Chem. A 3, 21733–21743 (2015)

25.

S.Y. Qu, C. Qin, A. Islam, Y.Z. Wu, W.H. Zhu, J.L. Hua, H. Tian, L.Y. Han, Chem. Commun. 48, 6972–6974 (2012)

26.

S.S. Li, K.-J. Jiang, F. Zhang, J.-H. Huang, S.-G. Li, M.-G. Chen, L.-M. Yang, Y.-L. Song, Org. Electron. 15, 1579–1585 (2014)

27.

H. Li, Y. Wu, Z. Geng, J. Liu, D. Xu, W. Zhu, J. Mater. Chem. A 2, 14649–14657 (2014)

28.

H. Zhu, Y. Wu, J. Liu, W. Zhang, W. Wu, W.-H. Zhu, J. Mater. Chem. A 3, 10603–10609 (2015)

29.

K. Kakiage, Y. Aoyama, T. Yano, T. Otsuka, T. Kyomen, M. Unnoc, M. Hanaya, Chem. Commun. 50, 6379–6381 (2014)

30.

L.-L. Tan, J.-F. Huang, Y. Shen, L.-M. Xiao, J.-M. Liu, D.-B. Kuanga, C.-Y. Su, J. Mater. Chem. A 2, 8988–8994 (2014)

31.

S.S. Soni, K.B. Fadadu, J.V. Vaghasiya, B.G. Solanki, K.K. Sonigara, A. Singh, D. Das, P.K. Iyer, J. Mater. Chem. A 3, 21664–21671 (2015)

32.

X. Qian, Y.-Z. Zhu, W.-Y. Chang, J. Song, B. Pan, L. Lu, H.-H. Gao, J.-Y. Zheng, ACS Appl. Mater. Interfaces 7, 9015–9022 (2015)

33.

X. Yang, J. Zhao, L. Wang, J. Tiana, L. Suna, RSC Adv. 4, 24377–24383 (2014)

34.

M. Mao, X.-L. Zhang, X.-Q. Fang, G.-H. Wu, S.-Y. Dai, Q.-H. Song, X.-X. Zhang, J. Power Sources 268, 965–976 (2014)

35.

A. Baheti, K.R.J. Thomas, C.-T. Li, C.-P. Lee, K.-C. Ho, ACS Appl. Mater. Interfaces 7, 2249–2262 (2015)

36.

Z. Iqbal, W.-Q. Wu, Z.-S. Huang, L. Wang, D.-B. Kuang, H. Meier, D. Cao, Dyes Pigm. 124, 63–71 (2016)

37.

H. Lee, S.B. Yuk, J. Choi, H.J. Kim, H.W. Kim, S.H. Kim, B. Kim, M.J. Ko, J.P. Kim, Dyes Pigm. 102, 13–21 (2014)

38.

J. Li, X. Yang, M. Cheng, M. Wang, L. Sun, Dyes Pigm. 116, 58–64 (2015)

39.

Y.-F. Chen, J.-M. Liu, J.-F. Huang, L.-L. Tan, Y. Shen, L.-M. Xiao, D.-B. Kuang, C.-Y. Su, J. Mater. Chem. A 3, 8083–8090 (2015)

40.

K. Ogawa, S.C. Rasmussen, J. Org. Chem. 68, 2921–2928 (2003)

41.

S.C. Rasmussen, S.J. Evenson, Prog. Polym. Sci. 38, 1773–1804 (2013)

42.

J. Zhang, Z. Yao, Y. Cai, L. Yang, M. Xu, R. Li, M. Zhang, X. Donga, P. Wang, Energy Environ. Sci. 6, 1604–1614 (2013)

43.

N. Cai, J. Zhang, M. Xu, M. Zhang, P. Wang, Adv. Funct. Mater. 23, 3539–3547 (2013)

44.

Z. Wang, M. Liang, L. Wang, Y. Hao, C. Wang, Z. Sun, S. Xue, Chem. Commun. 49, 5748–5750 (2013)

45.

Z. Wang, H. Wang, M. Liang, Y. Tan, F. Cheng, Z. Sun, ACS Appl. Mater. Interfaces 6, 5768–5778 (2014)

46.

Z. Wang, M. Liang, Y. Tan, L. Ouyang, Z. Suna, S. Xue, J. Mater. Chem. A 3, 4865–4874 (2015)

47.

S. Kumar, K.R.J. Thomas, C.-T. Li, K.-C. Ho, Org. Electron. 26, 109–116 (2015)

48.

Y. Xie, W. Wu, H. Zhu, J. Liu, W. Zhang, H. Tian, W.-H. Zhu, Chem. Sci. 7, 544–549 (2016)

49.

D. Sahu, H. Padhy, D. Patra, J.-F. Yin, Y.-C. Hsu, J.-T. Lin, K.-L. Lu, K.-H. Wei, H.-C. Lin, Tetrahedron 67, 303–311 (2011)

50.

P. Dai, L. Yang, M. Liang, H. Dong, P. Wang, C. Zhang, Z. Sun, S. Xue, ACS Appl. Mater. Interfaces 7, 22436–22447 (2015)

51.

N. Miyaura, A. Suzuki, Chem. Rev. 95, 2457–2483 (1995)

52.

J.K. Stille, Angew. Chem. Int. Ed. 25, 508–524 (1986)

53.

E. Knoevenagel, Chem. Ber. 29, 172 (1896)

54.

J. Liu, R. Zhang, G. Sauvé, T. Kowalewski, R.D. McCullough, J. Am. Chem. Soc. 130, 13167–13176 (2008)

55.

D.G.D. Patel, F. Feng, Y. Ohnishi, K.A. Abboud, S. Hirata, K.S. Schanze, J. Am. Chem. Soc. 134, 2599–2612 (2012)

56.

C. Reichardt, Chem. Rev. 94, 2319–2358 (1994)

57.

A. Granzhan, H. Ihmels, G. Viola, J. Am. Chem. Soc. 129, 1254–1267 (2007)

58.

K. Sayama, S. Tsukagoshi, K. Hara, Y. Ohga, A. Shinpou, Y. Abe, S. Suga, H. Arakawa, J. Phys. Chem. B 106, 1363–1371 (2002)

59.

H. Raghuraman, D.A. Kelkar, A. Chattopadhyay, in Reviews in Fluorescence 2005, ed. by C.D. Geddes, J. R. Lakowicz (Springer, New York, 2005), p. 199

60.

N. Blouin, A. Michaud, D. Gendron, S. Wakim, E. Blair, R. Neagu-Plesu, M. Belletete, G. Durocher, Y. Tao, M. Leclerc, J. Am. Chem. Soc. 130, 732–742 (2007)

61.

M. Grätzel, Nature 414, 338–344 (2001)

62.

A.N.M. Green, E. Palomares, S.A. Haque, J.M. Kroon, J.R. Durrant, J. Phys. Chem. B 109, 12525–12533 (2005)

63.

D. Sholl, J.A. Steckel, Density Functional Theory: A Practical Introduction (Wiley-VCH, Somerset, 2009)

64.

W. Koch, M.C. Holthausen, A Chemist’s Guide to Density Functional Theory (Wiley-VCH, Weinheim, 2000)

65.

S.-Q. Fan, Y. Geng, C. Kim, S. Paik, J. Ko, Mater. Chem. Phys. 132, 943–949 (2012)

66.

J.-H. Yum, S.R. Jang, R. Humphry-Baker, M. Grätzel, J.-J. Cid, T. Torres, M.K. Nazeeruddin, Langmuir 24, 5636–5640 (2008)

67.

P. Bonhôte, J.-E. ; Moser, R. Humphry-Baker, N. Vlachopoulos, S.M. Zakeeruddin, L. Walde, M. Grätzel, J. Am. Chem. Soc. 121, 1324–1336 (1999)

68.

W. Ying, F. Guo, J. Li, Q. Zhang, W. Wu, H. Tian, J. Hua, ACS Appl. Mater. Interfaces 4, 4215–4224 (2012)

69.

S. Qu, B. Wang, F. Guo, J. Li, W. Wu, C. Kong, Y. Long, J. Hua, Dyes Pigm. 92, 1384–1393 (2012)

70.

I. Mora-Seró, S. Giménez, F. Fabregat-Santiago, R. Gòmez, Q. Shen, T. Toyoda, Acc. Chem. Res. 42, 1848–1857 (2009)

71.

J. Van de Lagemaat, N.-G. Park, A.J. Frank, J. Phys. Chem. B 104, 2044–2052 (2000)

Title: Effect of electron-deficient linkers on the physical and photovoltaic properties of dithienopyrrole-based organic dyes
Authors: Sunil Kumar
K. R. Justin Thomas
Chun-Ting Li
Kuo-Chuan Ho
Publication date: 30-08-2017
Publisher: Springer US
Published in: Journal of Materials Science: Materials in Electronics / Issue 24/2017
Print ISSN: 0957-4522
Electronic ISSN: 1573-482X
DOI: https://doi.org/10.1007/s10854-017-7787-4

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