Solvatochromism in Diketopyrrolopyrrole Derivatives: Experimental and Computational Studies
Rebecca S. Szabadai A , Jesse Roth-Barton A , Kenneth P. Ghiggino A C , Jonathan M. White A C and David J. D. Wilson BA School of Chemistry and BIO-21 Institute, The University of Melbourne, Melbourne, Vic. 3010, Australia.
B Department of Chemistry, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Vic. 3086, Australia.
C Corresponding authors. Email: ghiggino@unimelb.edu.au; whitejm@unimelb.edu.au
Australian Journal of Chemistry 67(9) 1330-1337 https://doi.org/10.1071/CH14057
Submitted: 6 February 2014 Accepted: 8 May 2014 Published: 5 June 2014
Abstract
A series of seven thiophen-substituted diketopyrrolopyrrole derivatives were synthesised and their solution absorption spectra characterised in a range of solvents of varying polarity. The absorption spectra of these diketopyrrolopyrrole derivatives exhibited significant negative solvatochromism. The behaviour is consistent with results of time-dependent density-functional theory calculations of excitation energies. Calculated electronic structures suggest that there is significant charge transfer between the electron-donating thiophen substituents and the diketopyrrolopyrrole core but that the magnitude of this charge shift is reduced in the excited state compared with the ground state. The resulting reduction in polarity of the excited state accounts for the negative solvatochromism observed. The implications of the results for the potential application of diketopyrrolopyrrole compounds as photovoltaic materials are considered.
References
[1] Z. Hao, A. Izqbal, Chem. Soc. Rev. 1997, 26, 203.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXlt1Wmurg%3D&md5=3fcd9911e645ca5fb5bc22a63a225f9eCAS |
[2] K. Zhang, New Conjugated Polymers Based on Benzodifuranone and Diketopyrrolopyrrole 2010 (Universität zu Koln: Cologne).
[3] (a) A. B. Tamayo, M. Tantiwiwat, B. Walker, T.-Q. Nguyen, J. Phys. Chem. C 2008, 112, 15543.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtVymtbfM&md5=17f2be88aee808436763294a32761092CAS |
(b) A. B. Tamayo, B. Walker, T.-Q. Nguyen, J. Phys. Chem. C 2008, 112, 11545.
| Crossref | GoogleScholarGoogle Scholar |
(c) J. Peet, A. B. Tamayo, X. D. Dang, J. H. Seo, T.-Q. Nguyen, Appl. Phys. Lett. 2008, 93, 163306.
| Crossref | GoogleScholarGoogle Scholar |
(d) S. Lunak, L. Havel, J. Vynuchai, P. Horakova, J. Kucerok, M. Weiter, R. Hrdina, Dyes Pigments 2010, 85, 27.
| Crossref | GoogleScholarGoogle Scholar |
(e) S. Lunak, M. Vala, J. Vynuchai, I. Ouzzane, P. Horakova, P. Moziskova, Z. Elias, M. Weiter, Dyes Pigments 2011, 91, 269.
| Crossref | GoogleScholarGoogle Scholar |
(f) M. Kaur, D. S. Yang, K. Choi, M. J. Cho, D. H. Choi, Dyes Pigments 2014, 100, 118.
| Crossref | GoogleScholarGoogle Scholar |
(g) J. Liu, Y. Sun, P. Moosin, M. Kuik, C. M. Proctor, J. Lin, B. B. Hsu, V. Promarak, A. J. Heeger, T.-Q. Nguyen, Adv. Mater. 2013, 25, 5898.
| Crossref | GoogleScholarGoogle Scholar |
(h) C. Kim, J. Liu, J. Lin, A. B. Tamayo, B. Walker, G. Wu, T.-Q. Nguyen, Chem. Mater. 2012, 24, 1699.
| Crossref | GoogleScholarGoogle Scholar |
[4] O. Wallquist, R. Lenz, Macromol. Symp. 2002, 187, 617.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XntVSgu7Y%3D&md5=13dc1128a48d49319efb8544c3a26e83CAS |
[5] (a) C. Reichardt, Solvents and Solvent Effects in Organic Chemistry 2002 (Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim).
(b) C. Reichardt, Chem. Rev. 1994, 94, 2319.
| Crossref | GoogleScholarGoogle Scholar |
[6] A. B. Pangborn, M. A. Giardello, R. H. Grubbs, R. K. Rosen, F. J. Timmers, Organometallics 1996, 15, 1518.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XhtVerur0%3D&md5=4c85af8f7bf828fa87c4b71d3c146c7fCAS |
[7] W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1cXksF2hu7s%3D&md5=ba4f73187c8b5ca6624407e6ba1c2f23CAS |
[8] T. D. M. Bell, K. P. Ghiggino, A. Haynes, S. J. Langford, C. P. Woodward, J. Porphyr. Phthalocyanines 2007, 11, 455.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXotVylu7w%3D&md5=d505ba4f257edff0f76103b605400f13CAS |
[9] M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian 09, Revision D.1 2009 (Gaussian, Inc.: Wallingford, CT).
[10] (a) A. D. Becke, Phys. Rev. A 1988, 38, 3098.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXmtlOhsLo%3D&md5=89a4d6eea189a0acadf44cab2961b4a3CAS | 9900728PubMed |
(b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
| Crossref | GoogleScholarGoogle Scholar |
(c) A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
| Crossref | GoogleScholarGoogle Scholar |
[11] J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXmsVynurc%3D&md5=56defe400410427bc5df2a020f39d1d6CAS | 16092826PubMed |
[12] C. Adamo, V. Barone, J. Chem. Phys. 1998, 108, 664.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXhvF2ntw%3D%3D&md5=8104539f4afde6b61541270626b8879dCAS |
[13] J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett. 1997, 78, 1396.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXht1Gns7o%3D&md5=6b82347f04c4a2e97344d91a16a0e61cCAS |
[14] J.-D. Chai, M. Head-Gordon, Phys. Chem. Chem. Phys. 2008, 10, 6615.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtlCksbfO&md5=b65571635ddde35df4e28a9d8c46aa76CAS | 18989472PubMed |
[15] S. I. Gorelsky, AOMix: Program for Molecular Orbital Analysis, Version 6.46 2010 (University of Ottawa: Ottawa, ON). Available at http://www.sg-chem.net/
[16] A. B. Tamayo, X.-D. Dang, B. Walker, J. Seo, T. Kent, T.-Q. Nguyen, Appl. Phys. Lett. 2009, 94, 103301.
| Crossref | GoogleScholarGoogle Scholar |
[17] A. Zulauf, M. Mellah, R. Guillot, E. Schulz, Eur. J. Org. Chem. 2008, 2118.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXltlygsbw%3D&md5=c6b374d8d66683cb60694d81f6e1f7a8CAS |
