Geometric and Electronic Structure and Optical Response of Oligo‐ and Polythiophenes: Relation to Their Use in Electro‐optic and Photonic Devices

Cornil, Jérôme; Beljonne, David; Parenté, V.; Lazzaroni, Roberto; Brédas, Jean‐Luc

doi:10.1002/9783527611713.ch6

Cited by 8 publications

(6 citation statements)

References 150 publications

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“…There is quite a lot of literature devoted to the study of specific properties, in particular optical properties of polymers of the P3HT family. Most of these studies were performed using experimental methods. ,,− Theoretical methods represent a valuable tool to discuss how aggregation affects the optical properties of P3HT species, offering guidelines to engineer materials with enhanced desired properties. In this framework and despite the huge knowledge gained by previous studies using basic or more sophisticated models, ,,− we have undertaken theoretical calculations using modern DFT-based methods.…”

Section: Introductionmentioning

confidence: 99%

Revisiting the Vibrational and Optical Properties of P3HT: A Combined Experimental and Theoretical Study

et al. 2018

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We demonstrate that DFT-based calculations can provide straightforward means to analyze the effect of aggregation on the optical properties of regioregular P3HT oligomers of different lengths (up to 20-mers) and of bioligomers of 8-mers in two different conformations. Our conclusions substantially differ from those obtained previously by applying the exciton model. Indeed, analysis of Huang-Rhys factors has evidenced that two vibrational modes, a collective mode and an effective mode, are combined in the vibronic structure of the absorption spectrum of oligothiophene. Computed spectra match perfectly their experimental counterparts provided we consider that the oligomer and at least the five lowest excited states of bioligomers behave as absorbers, and that both oligomer and bioligomer contribute to the emission spectra. Study of the nature of the Franck-Condon excitation and optimization of the five lowest excited singlet states indicate that high (hot) excited states of the bioligomer may play an important role in the initiation of charge separation and highlight the importance to take into account the relaxation processes in the theoretical modeling of emission properties.

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Section: Introductionmentioning

confidence: 99%

Revisiting the Vibrational and Optical Properties of P3HT: A Combined Experimental and Theoretical Study

et al. 2018

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“…Besides, a large number of experimental studies are devoted to the designing of new thiophene materials, a number of pertinent theoretical studies have also been made on these materials. [42][43][44][45][46][47][48][49][50][51][52][53][54] However, an understanding of the properties of these materials still forms a pre-requisite for further development. In view of this, herein, we have attempted to understand the reactivity, aromaticity, and absorption spectra of few fused thiophene oligomers.…”

Section: Introductionmentioning

confidence: 99%

Does oligomerization in fused thiophene affect reactivity and aromaticity?

Bhattacharyya¹

2016

J Chem Sci

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Reactivity and aromaticity of a few fused thiophene oligomers and their conformers are discussed in the light of density functional theory (DFT) and conceptual density functional theory. Reactivity parameters, such as hardness (η) and electrophilicity (ω), chemical potential (μ) and energy of the HOMO (highest occupied molecular orbital) have been studied. Oligomerization raises the E HOMO of the species, which in turn increases the reactivity of the oligomers. The absorption spectra of the species are analysed using TDDFT (time dependent density functional theory). The absorption peaks show red shift with increasing size of the oligomers. Aromaticity of the species is gauged by nucleus independent chemical shift (NICS). The out-of-plane component, (NICS zz) values advocate higher aromatic character at longer distance whereas, NICS supports the reverse.

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“…Nanoscale molecular wires are usually constructed from linked conjugated units from the class called aromatic systems. Examples of aromatic compounds include benzene (1) and thiophene (2), molecules with six conjugated pi electrons in a single ring. Such systems have exceptional stability, because the pi electrons comprise a filled molecular shell; filled shells are also exceptionally stable in atoms (the rare gases) and in nuclei (nuclear shell theory).…”

Section: Introductionmentioning

confidence: 99%

Charge transport in nanoscale aromatic and antiaromatic systems

Breslow

Foss

2008

J. Phys.: Condens. Matter

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Molecules such as benzene, that have six pi electrons cyclically delocalized, have the special stability that chemists call aromaticity. When electricity passes through a molecular wire containing a benzene ring a quinone-like structure is induced, and there is some loss of aromaticity. The conductance of such systems correlates with the magnitude of this effect. A molecule such as cyclobutadiene with only four cyclically delocalized pi electrons has special instability, called antiaromaticity. Evidence that such antiaromatic systems could convey high conductance in appropriate systems is derived from electrochemical studies, which also detect geometric changes in some thiophene-derived nanolength wires.

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Geometric and Electronic Structure and Optical Response of Oligo‐ and Polythiophenes: Relation to Their Use in Electro‐optic and Photonic Devices

Cited by 8 publications

References 150 publications

Revisiting the Vibrational and Optical Properties of P3HT: A Combined Experimental and Theoretical Study

Revisiting the Vibrational and Optical Properties of P3HT: A Combined Experimental and Theoretical Study

Does oligomerization in fused thiophene affect reactivity and aromaticity?

Charge transport in nanoscale aromatic and antiaromatic systems

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