Computational engineering of low bandgap copolymers

Frontiers in Chemistry

Volumn 1, Issue , 2013, Pages

  Wykes, Michael ^a   Milián Medina, Begoña ^a   Gierschner, Johannes ^a  

^a INSTITUTO MADRILEÑO DE ESTUDIOS AVANZADOS EN NANOCIENCIA IMDEA NANOCIENCIA   (Spain)

Author keywords

Conjugated materials; Density functional theory; Donor acceptor copolymers; Low bandgap polymers; Optical bandgaps; Polymer extrapolation; Quantum chemistry

Indexed keywords

EID: 84987739797     PISSN: None     EISSN: 22962646     Source Type: Journal    
DOI: 10.3389/fchem.2013.00035     Document Type: Article

References (75)

1. Ajayaghosh, A. (2003). Donor-acceptor type low band gap polymers: polysquaraines and related systems. Chem. Soc. Rev. 32, 181-191. doi: 10.1039/b204251g
2. Beaujuge, P. M., Amb, C. M., and Reynold, J. R. (2010). Spectral engineering in π-conjugated polymers with intramolecular donor-acceptor interactions. Acc. Chem. Res. 43, 1396-1407. doi: 10.1021/ar100043u
3. Becke, A. D. (1993a). A new mixing of Hartree-Fock and local density-functional theories. J. Chem. Phys. 98, 1372-1377. doi: 10.1063/1.464304
4. Becke, A. D. (1993b). Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-5652. doi: 10.1063/1.464913
5. Bérubé, N., Gosselin, V., Gaudreau, J., and Côté, M. (2013). Designing polymers for Photovoltaic applications using ab initio calculations. J. Phys. Chem. C 117, 7964-7972. doi: 10.1021/jp309800f
6. Blouin, N., Michaud, A., Gendron, D., Wakim, S., Plesu, R., Belletête, M., et al. (2008). Toward a rational design of poly(2,7-carbazole) derivatives for solar cells. J. Am. Chem. Soc. 130, 732-742. doi: 10.1021/ja0771989
7. Brédas, J. L., Norton, J. E., Cornil, J., and Coropceanu, V. (2009). Molecular understanding of organic solar cells: the challenges. Acc. Chem. Res. 42, 1691-1699. doi: 10.1021/ar900099h
8. Bundgaard, E., and Krebs, F. C. (2007). Low band gap polymers for organic photovoltaics. Sol. Energy Mater. Sol. Cells 91, 954-985. doi: 10.1016/j.solmat.2007.01.015
9. Carsten, B., Szarko, J. M., Son, H. J., Wang, W., Lu, L., He, F., et al. (2011). Examining the effect of the dipole moment on charge separation in donoracceptor polymers for organic photovoltaic applications. Am. Chem. Soc. 133, 20468-20475. doi: 10.1021/ja208642b
10. Chen, J., and Cao, Y. (2009). Development of novel conjugated donor polymers for high-efficiency bulk-heterojunction photovoltaic devices. Acc. Chem. Res. 42, 1709-1718. doi: 10.1021/ar900061z
11. Chen, L.-M., Hong, Z., Li, G., and Yan, Y. (2009). Recent progress in polymer solar cells: manipulation of polymer:fullerene morphology and the formation of efficient inverted polymer solar cells. Adv. Mater. 21, 1434-1449. doi: 10.1002/adma.200802854
12. Chen, W. C., and Jenekhe, S. A. (1995). Small-bandgap conducting polymers based on conjugated poly(heteroary1ene methines). 1. Precursor poly(heteroary1ene methylenes). Macromolecules 28, 454-464. doi: 10.1021/ma00106a008
13. Cheng, Y.-J., Yang, S.-H., and Hsu, C.-S. (2009). Synthesis of conjugated polymers for organic solar cell applications. Chem. Rev. 109, 5868-5923. doi: 10.1021/cr900182s
14. Cohen, A. J., Mori-Sánchez, P., and Yang, W. (2012). Challenges for density functional theory. Chem. Rev. 112, 289-320. doi: 10.1021/cr200107z
15. Cornil, J., Gueli, I., Dkhissi, A., C., Sancho-Garcia, J., Hennebicq, E., Calbert, J. P., et al. (2003). Electronic and optical properties of polyfluorene and fluorene-based copolymers: a quantum-chemical characterization. J. Chem. Phys. 118, 6615-6623. doi: 10.1063/1.1561054
16. Coughlin, J., Henson, Z. B., Welch, G. C., and Bazan, G. C. (2013) Design and synthesis of molecular donors for solution-processed high-efficiency organic solar cells. Acc. Chem. Res. doi: 10.1021/ar400136b. [Epub ahead of print].
17. Dreuw, A., and Head-Gordon, M. (2004). Failure of time-dependent density functional theory for long-range charge-transfer excited states: the zincbacteriochlorin-bacteriochlorin and Bbacteriochlorophyll-spheroidene complexes. J. Am. Chem. Soc. 126, 4007-4016. doi: 10.1021/ja039556n
18. Dutta, T., Woody, K. B., Parkin, S. R., Watson, M. D., and Gierschner, J. (2009). Conjugated polymers with large effective Stokes shift: benzobisdioxole-based poly(phenyleneethynylene)s. J. Am. Chem. Soc. 131, 17321-17327. doi: 10.1021/ja9068134
19. Egelhaaf, H.-J., Gierschner, J., and Oelkrug, D. (2002). Polarizability effects and energy transfer in quinquethiophene doped bithiophene and OPV films. Synth. Met. 127, 221-227. doi: 10.1016/S0379-6779(01)00627-0
20. Flukiger, P., Luthi, H. P., Portmann, S., and Weber, J. (2000-2002.) MOLEKEL: an Interactive Molecular Graphics Tool, Swiss Center for Scientific Computing. Manno.
21. Foster, M. E., and Wong, B. M. (2012). Nonempirically tuned range-separated DFT accurately predicts both fundamental and excitation gaps in DNA and RNA nucleobases. J. Chem. Theory Comput. 8, 2682-2687. doi: 10.1021/ct300420f
22. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., et al. (2009). Gaussian 09. Wallingford, CT: Gaussian, Inc.
23. Gierschner, J., Cornil, J., and Egelhaaf, H.-J. (2007). Optical bandgaps of p-conjugated organic materials at the polymer limit: experiment and theory. Adv. Mater. 19, 173-191. doi: 10.1002/adma.200600277
24. Gierschner, J., Egelhaaf, H.-J., Mack, H.-G., Schweizer, S., Doser, B., and Oelkrug, D. (2003). Optical spectra of oligothiophenes: vibronic states, torsional motions, and solvent shifts. Synth. Met. 138, 311-315. doi: 10.1016/S0379-6779(03)00030-4
25. Gierschner, J., Huang, Y.-S., Van Averbeke, B., Cornil, J., Friend, R. H., and Beljonne, D. (2009). Exciton versus electronic couplings in molecular assemblies: the importance of non-nearest neighbour interactions. J. Chem. Phys. 130, 044105. doi: 10.1063/1.3065267
26. Gierschner, J., Mack, H.-G., Lüer, L., and Oelkrug, D. (2002). Fluorescence and absorption spectra of oligophenylenevinylenes: vibronic coupling, band shapes and solvatochromism. J. Chem. Phys. 116, 8596-8609. doi: 10.1063/1.1469612
27. Gil-Bernal, H., Zambrano, M. L. and Arce, J. C. (2010). Quantum-chemical-aided design of copolymers with tailored bandgaps and effective masses: the role of composition. Int. J. Quantum Chem. 110, 2522-2531. doi: 10.1002/qua.22714
28. Hachmann, J., Olivares-Amaya, R., Atahan-Evrenk, S., Amador-Bedolla, C., Saìnchez-Carrera, R. S., Gold-Parker, A. et al. (2011). The Harvard clean energy project: large-scale computational screening and design of organic photovoltaics on the world community grid. J. Phys. Chem. Lett. 2, 2241-2251. doi: 10.1021/jz200866s
29. Havinga, E. E., ten Hoeve, W., and Wynberg, H. (1993). Alternate donor-acceptor small-band-gap semiconducting polymers; Polysquaraines and polycroconaines. Synth. Met. 55-57, 299-306. doi: 10.1016/0379-6779(93)90949-W
30. Huang, Y.-S., Gierschner, J., Schmidtke, J. P., Friend, R. H., and Beljonne, D. (2011). Tuning interchain and intrachain interactions in polyfluorene copolymers. Phys. Rev. B. 84, 205311. doi: 10.1103/PhysRevB.84.205311
31. Hung, Y.-C., Chao, C.-Y., Dai, C.-A., Su, W.-F., and Lin, S.-T. (2013). Band gap engineering via controlling donor-acceptor compositions in conjugated copolymers. J. Phy. Chem. B. 117, 690-696. doi: 10.1021/jp3090974
32. Jacquemin, D., Femenias, A., Chermette, H., Ciofini, I., Adamo, C., Andre, J. M., et al. (2006). Assessment of several hybrid DFT functionals for the evaluation of bond length alternation of increasingly long oligomers. J. Phys. Chem. A 110, 5952-5959. doi: 10.1021/jp060541w
33. Kanal, I. Y., Owens, S. G., Bechtel, J. S., and Hutchison, G. R. (2013). Efficient computational screening of organic polymer photovoltaics. J. Phys. Chem. Lett. 4, 1613-1623. doi: 10.1021/jz400215j
34. Karsten, B. P., and Janssen, R. A. J. (2011). Chain length dependence in diketopyrrolopyrrole/thiophene oligomers. Macromol. Chem. Phys. 212, 515-520. doi: 10.1002/macp.201000695
35. Karsten, B. P., Viani, L., Gierschner, J., Cornil, J., and Janssen, R. A. J. (2008). An oligomer study to small bandgap polymers. J. Phys. Chem. A 112, 10764-10773. doi: 10.1021/jp805817c
36. Karsten, B. P., Viani, L., Gierschner, J., Cornil, J., and Janssen, R. A. J. (2009). On the origin of small band gaps in alternating thiophene-thienopyrazine oligomers. J. Phys. Chem. A 11, 10343-10350. doi: 10.1021/jp9050148
37. Kertesz, M., Choi, C. H., and Yang, S. (2005). Conjugated polymers and aromaticity. Chem. Rev. 105, 3448-3481. doi: 10.1021/cr990357p
38. Körzdörfer, T., Parrish, R. M., Sears, J. S., Sherrill, C. D., and Brédas, J. L. (2012). On the relationship between bond-length alternation and many-electron self-interaction error. J. Chem. Phys. 137, 124305. doi: 10.1063/1.4752431
39. Körzdörfer, T., Sears, J. S., Sutton, C., and Brédas, J. L. (2011). Long-range corrected hybrid functionals for p-conjugated systems: dependence of the range-separation parameter on conjugation length. J. Chem. Phys. 135, 204107. doi: 10.1063/1.3663856
40. Kroon, R., Lenes, M., Hummelen, J. C., Blom, P. W. M., and de Boer, B. (2008). Small bandgap polymers for organic solar cells (polymer material development in the last 5 years). Polymer Rev. 48, 531-582. doi: 10.1080/15583720802231833
41. Kuhn, W. (1948). über das Absorptionsspektrum der Polyene. Helv. Chim. Acta 31, 1780-1799. doi: 10.1002/hlca.19480310644
42. Kürti, J., and Surján, P. R. (1990). Quinoid vs aromatic structure of polyisothianaphthene. J. Chem. Phys. 92, 3247-3248. doi: 10.1063/1.457883
43. Li, Y. (2012). Molecular design of photovoltaic materials for polymer solar cells: toward suitable electronic energy levels and broad absorption. Acc. Chem. Res. 45, 723-733. doi: 10.1021/ar2002446
44. Longo, L., Carbonera, C., Pellegrino, A., Perin, N., Schimperna, G., Tacca, A., et al. (2012). Comparison between theoretical and experimental electronic properties of some popular donor polymers for bulk-heterojunction solar cells. Sol. Energy Mater. Sol. Cells 97, 139-149. doi: 10.1016/j.solmat.2011.09.035
45. Macchi, G., Milián Medina, B., Zambianchi, M., Tubino, R., Cornil, J., Barbarella, G., et al. (2009). Spectroscopic signatures for planar equilibrium geometries in methyl-substituted oligothiophenes. Phys. Chem. Chem. Phys. 11, 984-990. doi: 10.1039/b810915j
46. Meier, H. (2005). Conjugated oligomers with terminal donor-acceptor substitution. Angew. Chem. Int. Ed. 44, 2482-2506. doi: 10.1002/anie.200461146
47. Meier, H., Stalmach, U., and Kolshorn, H. (1997). Effective conjugation length and UV/vis spectra of oligomers. Acta Polym. 48, 379-384. doi: 10.1002/actp.1997.010480905
48. Milián-Medina, B., and Gierschner, J. (2012a). π-Conjugation. WIREs Comput. Mol. Sci. 2, 513-524. doi: 10.1002/wcms.95
49. Milián-Medina, B., and Gierschner, J. (2012b). Computational design of low singlet-triplet gap all-organic molecules for OLED application. Org. Electron. 13, 895-911. doi: 10.1016/j.orgel.2012.02.010
50. Milián Medina, B., Van Vooren, A., Brocorens, P., Gierschner, J., Shkunov, M., Heeney, M., et al. (2007). Electronic structure and charge transport properties of polythiophene chains containing thienothiophene units: a joint experimental and theoretical study. Chem. Mater. 19, 4949-4956. doi: 10.1021/cm071279m
51. Milián-Medina, B., Varghese, S., Ragni, R., Boerner, H., Ortí, E., Farinola, G. M., et al. (2011). Excited state switching by per-fluorination of para-oligophenylenes. J. Chem. Phys. 135, 124509. doi: 10.1063/1.3643151
52. Milián Medina, B., Wasserberg, D., Meskers, S. C. J., Mena-Osteritz, E., Bäuerle, P., and Gierschner, J. (2008). EDOT-type materials: planar but not rigid. J. Phys. Chem. A 112, 13282-13286. doi: 10.1021/jp809632z
53. Müllen, K., and Wegner, G. (1998). Electronic Materials: the Oligomer Approach. Weinheim: Wiley-VCH. doi: 10.1002/9783527603220
54. Özen, A. S., Atilgan, C., and Sonmez, G. (2007). Noncovalent intramolecular interactions in the monomers and oligomers of the acceptor and donor type of low band gap conducting polymers. J. Phys. Chem. C 111, 16362-16371. doi: 10.1021/jp074380n
55. Pappenfus, T. M., Burand, M. W., Janzen, D. E., and Mann, K. R. (2003). Synthesis and characterization of tricyanovinyl-capped oligothiophenes as low-band-gap organic materials. Org. Lett. 5, 1535-1538. doi: 10.1021/ol034317q
56. nCN (n = 1-6). J. Phys. Chem. B 11, 6499-6505. doi: 10.1021/jp055455v
57. Ponce Ortiz, R., Casado, J., Hernández, V., López Navarrete, J. T., Viruela, P. M., Ortí, E., et al. (2007). On the biradicaloid nature of long quinoidal oligothiophenes: experimental evidence guided by theoretical studies. Angew. Chem. Int. Ed. 46, 9057-9061. doi: 10.1002/anie.200703244
58. Raos, G., Famulari, A., and Marcon, V. (2003). Computational reinvestigation of the bithiophene torsion potential. Chem. Phys. Lett. 379, 364-372. doi: 10.1016/j.cplett.2003.08.060
59. Risko, C., McGehee, M. D., and Brédas, J. L. (2011). A quantum-chemical perspective into low optical-gap polymers for highly-efficient organic solar cells. Chem. Sci. 2, 1200-1218. doi: 10.1039/C0SC00642D
60. Roncali, J. (1997). Synthetic principles for bandgap control in linear π-conjugated systems. Chem. Rev. 97, 173-206. doi: 10.1021/cr950257t
61. Salzner, U., and Köse, M. E. (2002). Does the donor-acceptor concept work for designing synthetic metals? 2. Theoretical investigation of copolymers of 4-(dicyanomethylene)-4H-cyclopenta[2,1-b:3,4-b']dithiophene and 3,4-(Ethylenedioxy)thiophene. J. Phys. Chem. B 106, 9221-9226. doi: 10.1021/jp020142a
62. Sancho-García, J. C., and Pérez-Jiménez, A. J. (2007). Improved accuracy with medium cost computational methods for the evaluation of bond length alternation of increasingly long oligoacetylenes. Phys. Chem. Chem. Phys. 9, 5874-5879. doi: 10.1039/b710330a
63. Schmidtke, J. P., Kim, J.-S., Gierschner, J., Silva, C., and Friend, R. H. (2007). Optical spectroscopy of a polyfluorene copolymer at high pressure: intra-and inter-molecular interactions. Phys. Rev. Lett. 99, 167401. doi: 10.1103/PhysRevLett.99.167401
64. Schulze, K., Uhrich, C., Schüppel, R., Leo, K., Pfeiffer, M., Brier, E., et al. (2006). Efficient vacuum-deposited organic solar cells based on a new low-bandgap oligothiophene and fullerene C60. Adv. Mater. 18, 2872-2875. doi: 10.1002/adma.200600658
65. Son, H. J., He, F., Carsten, B. and Yu, L. (2011). Are we there yet? Design of better conjugated polymers for polymer solar cells. J. Mater. Chem. 21, 18934-18945. doi: 10.1039/c1jm12388b
66. Stephens, P. J., Devlin, F. J., Chabalowski, C. F., and Frisch, M. J. (1994). Ab Initio Calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J. Phys. Chem. 98, 11623-11627. doi: 10.1021/j100096a001
67. Takimiya, K., Osaka, I., and Nakano, M. (2013). π-building blocks for organic electronics: revaluation of "inductive" and "resonance" effects of π-electron deficient units. Chem. Mater. doi: 10.1021/cm4021063
68. Torras, J., Casanovas, J., and Alemán, C. (2012). Reviewing extrapolation procedures of the electronic properties o the π-conjugated polymer limit. J. Phys. Chem. A 116, 7571-7583. doi: 10.1021/jp303584b
69. Veldman, D., Meskers, S. C. J., and Janssen, R. A. J. (2009). The energy of charge-transfer states in electron donor-acceptor blends: insight into the energy losses in organic solar cells. Adv. Funct. Mater. 19, 1939-1948. doi: 10.1002/adfm.200900090
70. Wen, L. Duck, B. C., Dastoor, P. C., and Rasmussen, S. C. (2008). Poly(2,3-dihexylthieno[3,4-b]pyrazine) via GRIM polymerization: simple preparation of a solution processable, low-band-gap conjugated polymer. Macromolecules 41, 4576-4578. doi: 10.1021/ma801057s
71. Yanai, T., Tew, D., and Handy, N. (2004). A new hybrid exchange-correlation functional using the Coulomb-attenuating method (CAM-B3LYP). Chem. Phys. Lett. 393, 51-57. doi: 10.1016/j.cplett.2004.06.011
72. Zade, S. S., Zamoshchik, N., and Bendikov, M. (2011). From short conjugated oligomers to conjugated polymers. Lessons from studies on long conjugated oligomers. Acc. Chem. Res. 44, 14-24. doi: 10.1021/ar1000555
73. Zerner, M. C. (1994). "Semiempirical Molecular Orbital Methods." Reviews in Computational Chemistry, Vol. 2, eds K. W. Lipkowitz and D. B. Boyd (New York, NY: VCH), 313. doi: 10.1002/9780470125793.ch8
74. Zhao, Y., and Truhlar, D. G. (2006). Density functional for spectroscopy: no long-range self-interaction error, good performance for Rydberg and charge-transfer states, and better performance on average than B3LYP for ground states. J. Phys. Chem. A 110, 13126-13130. doi: 10.1021/jp066479k
75. Zhou, H., Yang, L., and You, W. (2012). Rational design of high performance conjugated polymers for organic solar cells. Macromolecules 45, 607-632. doi: 10.1021/ma201648t