A design strategy for intramolecular singlet fission mediated by charge-transfer states in donor-acceptor organic materials

Nature Materials

Volumn 14, Issue 4, 2015, Pages 426-433

  Busby, Erik ^a,b   Xia, Jianlong ^a   Wu, Qin ^b   Low, Jonathan Z ^a   Song, Rui ^a   Miller, John R ^b   Zhu, X Y ^a   Campos, Luis M ^a   Sfeir, Matthew Y ^b  

^a Columbia University ^*  (United States)

^b BROOKHAVEN NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DESIGN; ELECTRONIC STRUCTURE; EXCITONS; MOLECULES; POLYMERS; SYNTHESIS (CHEMICAL);

CHARGE TRANSFER STATE; DESIGN CONSTRAINTS; DESIGN STRATEGIES; MULTIPLE EXCITON GENERATIONS; NEAREST-NEIGHBOUR COUPLING; ORGANIC MATERIALS; POPULATION TRANSFER; TRIPLET POPULATION;

CHARGE TRANSFER;

EID: 84925443913     PISSN: 14761122     EISSN: 14764660     Source Type: Journal    
DOI: 10.1038/nmat4175     Document Type: Article

References (47)

1. Yu, G., Gao, J., Hummelen, J. C., Wudl, F. & Heeger, A. J. Polymer photovoltaic cells: Enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science 270, 1789-1791 (1995).
2. Tang, C.W. Two-layer organic photovoltaic cell. Appl. Phys. Lett. 48, 183-185 (1986).
3. Gélinas, S. et al. Ultrafast long-range charge separation in organic semiconductor photovoltaic diodes. Science 343, 512-516 (2014).
4. Brédas, J-L., Norton, J. E., Cornil, J. & Coropceanu, V. Molecular understanding of organic solar cells: The challenges. Acc. Chem. Res. 42, 1691-1699 (2009).
5. Erb, T. et al. Correlation between structural and optical properties of composite polymer/fullerene films for organic solar cells. Adv. Funct. Mater. 15, 1193-1196 (2005).
6. Kim, J. Y. et al. Efficient tandem polymer solar cells fabricated by all-solution processing. Science 317, 222-225 (2007).
7. You, J. et al. A polymer tandem solar cell with 10.6% power conversion efficiency. Nature Commun. 4, 1446 (2013).
8. Small, C. E. et al. High-efficiency inverted dithienogermole-thienopyrrolodione-based polymer solar cells. Nature Photon. 6, 115-120 (2012).
9. Sun, Y. et al. Solution-processed small-molecule solar cells with 6.7% efficiency. Nature Mater. 11, 44-48 (2012).
10. Shockley, W. & Queisser, H. J. Detailed balance limit of efficiency of p-n junction solar cells. J. Appl. Phys. 32, 510-519 (1961).
11. Hanna, M. C. & Nozik, A. J. Solar conversion efficiency of photovoltaic and photoelectrolysis cells with carrier multiplication absorbers. J. Appl. Phys. 100, 074510 (2006).
12. Ehrler, B. et al. In situ measurement of exciton energy in hybrid singlet-fission solar cells. Nature Commun. 3, 1019 (2012).
13. Tritsch, J. R., Chan, W-L., Wu, X., Monahan, N. R. & Zhu, X. Y. Harvesting singlet fission for solar energy conversion via triplet energy transfer. Nature Commun. 4, 2679 (2013).
14. Congreve, D. N. et al. External quantum efficiency above 100% in a singlet-exciton-fission-based organic photovoltaic cell. Science 340, 334-337 (2013).
15. Johnson, J. C., Nozik, A. J. & Michl, J. The role of chromophore coupling in singlet fission. Acc. Chem. Res. 46, 1290-1299 (2013).
16. Smith, M. B. & Michl, J. Singlet fission. Chem. Rev. 110, 6891-6936 (2010).
17. Roberts, S. T. et al. Efficient singlet fission discovered in a disordered acene film. J. Am. Chem. Soc. 134, 6388-6400 (2012).
18. Yost, S. R. et al. A transferable model for singlet fission kinetics. Nature Chem. 6, 492-497 (2014).
19. Antognazza, M. R. et al. Ultrafast excited state relaxation in long-chain polyenes. Chem. Phys. 373, 115-121 (2010).
20. Kraabel, B., Hulin, D., Aslangul, C., Lapersonne-Meyer, C. & Schott, M. Triplet exciton generation, transport and relaxation in isolated polydiacetylene chains: Subpicosecond pump-probe experiments. Chem. Phys. 227, 83-98 (1998).
21. Musser, A. J. et al. Activated singlet exciton fission in a semiconducting polymer. J. Am. Chem. Soc. 135, 12747-12754 (2013).
22. Gradinaru, C. C. et al. An unusual pathway of excitation energy deactivation in carotenoids: Singlet-to-triplet conversion on an ultrafast timescale in a photosynthetic antenna. Proc. Natl Acad. Sci. USA 98, 2364-2369 (2001).
23. Papagiannakis, E. et al. Light harvesting by carotenoids incorporated into the B850 light-harvesting complex from rhodobacter sphaeroides R-26.1: Excited-state relaxation, ultrafast triplet formation, and energy transfer to bacteriochlorophyll. J. Phys. Chem. B 107, 5642-5649 (2003).
24. Johnson, J. C. et al. Toward designed singlet fission: Solution photophysics of two indirectly coupled covalent dimers of 1,3-diphenylisobenzofuran. J. Phys. Chem. B 117, 4680-4695 (2013).
25. Dell, E. J. & Campos, L. M. The preparation of thiophene-S, S-dioxides and their role in organic electronics. J. Mater. Chem. 22, 12945-12952 (2012).
26. Wei, S. et al. Bandgap engineering through controlled oxidation of polythiophenes. Angew. Chem. Int. Ed. 53, 1832-1836 (2014).
27. Beljonne, D., Yamagata, H., Brédas, J., Spano, F. & Olivier, Y. Charge-transfer excitations steer the Davydov splitting and mediate singlet exciton fission in pentacene. Phys. Rev. Lett. 110, 226402 (2013).
28. Berkelbach, T. C., Hybertsen, M. S. & Reichman, D. R. Microscopic theory of singlet exciton fission. I. General formulation. J. Chem. Phys. 138, 114102 (2013).
29. Berkelbach, T. C., Hybertsen, M. S. & Reichman, D. R. Microscopic theory of singlet exciton fission II. Application to pentacene dimers and the role of superexchange. J. Chem. Phys. 138, 114103 (2013).
30. Chan, W-L. et al. The quantum coherent mechanism for singlet fission: Experiment and theory. Acc. Chem. Res. 46, 1321-1329 (2013).
31. Chan, W-L. et al. Observing the multiexciton state in singlet fission and ensuing ultrafast multielectron transfer. Science 334, 1541-1545 (2011).
32. Chan, W-L., Ligges, M. & Zhu, X. Y. The energy barrier in singlet fission can be overcome through coherent coupling and entropic gain. Nature Chem. 4, 840-845 (2012).
33. Sharifzadeh, S., Darancet, P., Kronik, L. & Neaton, J. B. Low-energy charge-transfer excitons in organic solids from first-principles: The case of pentacene. J. Phys. Chem. Lett. 4, 2197-2201 (2013).
34. Zhou, H., Yang, L. & You, W. Rational design of high performance conjugated polymers for organic solar cells. Macromolecules 45, 607-632 (2012).
35. Kitamura, C., Tanaka, S. & Yamashita, Y. Design of narrow-bandgap polymers. Syntheses and properties of monomers and polymers containing aromatic-donor and o-quinoid-acceptor units. Chem.Mater. 8, 570-578 (1996).
36. Brédas, J. Relationship between band gap and bond length alternation in organic conjugated polymers. J. Chem. Phys. 82, 3808-3811 (1985).
37. Havinga, E., Ten Hoeve, W. & Wynberg, H. A new class of small band gap organic polymer conductors. Polym. Bull. 29, 119-126 (1992).
38. Szarko, J. M. et al. Electronic processes in conjugated diblock oligomers mimicking low band-gap polymers. Experimental and theoretical spectral analysis. J. Phys. Chem. B 114, 14505-14513 (2010).
39. Guo, J., Ohkita, H., Benten, H. & Ito, S. Near-IR femtosecond transient absorption spectroscopy of ultrafast polaron and triplet exciton formation in polythiophene films with different regioregularities. J. Am. Chem. Soc. 131, 16869-16880 (2009).
40. Mullen, K. M., Vengris, M. & van Stokkum, I. H. Algorithms for separable nonlinear least squares with application to modelling time-resolved spectra. J. Glob. Optim. 38, 201-213 (2007).
41. Van Stokkum, I. H., Larsen, D. S. & van Grondelle, R. Global and target analysis of time-resolved spectra. Biochim. Biophys. Acta 1657, 82-104 (2004).
42. Wishart, J. F., Cook, A. R. & Miller, J. R. The LEAF Picosecond Pulse Radiolysis Facility at Brookhaven National Laboratory. Rev. Sci. Instrum. 75, 4359-4366 (2004).
43. Head-Gordon, M., Grana, A. M., Maurice, D. &White, C. A. Analysis of electronic transitions as the difference of electron attachment and detachment densities. J. Phys. Chem. 99, 14261-14270 (1995).
44. Oliva, M. M. et al. Do [all]-S, S′-dioxide oligothiophenes show electronic and optical properties of oligoenes and/or of oligothiophenes? J. Am. Chem. Soc. 132, 6231-6242 (2010).
45. Amir, E. et al. Synthesis and characterization of soluble low-bandgap oligothiophene-[all]-S, S-dioxides-based conjugated oligomers and polymers. J. Polym. Sci. A 49, 1933-1941 (2011).
46. Sreearunothai, P. et al. Triplet transport to and trapping by acceptor end groups on conjugated polyfluorene chains. J. Phys. Chem. C 115, 19569-19577 (2011).
47. Heinzelmann, W. & Labhart, H. Triplet-triplet spectra and triplet quantum yields of some aromatic hydrocarbons in liquid solution. Chem. Phys. Lett. 4, 20-24 (1969).