Conformational and electronic properties of small benzothiadiazole-cored oligomers with aryl flanking units: Thiophene versus Furan

Raychev, Deyan; Guskova, Olga; Seifert, Gotthard; Sommer, Jens‐Uwe

doi:10.1016/j.commatsci.2016.09.044

Cited by 23 publications

(14 citation statements)

References 55 publications

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“…The absorption spectra are simulated employing Gaussian functions with GaussView5 default parameters for half of the width to build a continuous spectrum from a collection energies and oscillation strengths. The most calculations are performed with B3LYP/6‐31G* functional since it gives accurate geometries and the values of band gaps ( E g ), as seen in our previous studies …”

Section: Methodsmentioning

confidence: 99%

“…The most calculations are performed with B3LYP/6-31G* [58] functional since it gives accurate geometries and the values of band gaps (E g ), as seen in our previous studies. [47,59] The reorganization energies λ are obtained using the fourpoint formalism [47,60] as a difference of geometry relaxation energies upon going from neutral (0) to charged-state (AE) geometry:…”

Section: Methodsmentioning

confidence: 99%

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A comparative analysis of symmetric diketopyrrolopyrrole‐cored small conjugated molecules with aromatic flanks: From geometry to charge transport

et al. 2018

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Diketopyrrolopyrrole (DPP) derivatives are promising compounds for application in organic electronics. Here, we investigate several symmetrical N‐unsubstituted and N‐methyl substituted DPPs which differ in the heteroatom in the aromatic flanks. The conformational, electronic, and optical properties are characterized for single molecules in vacuum or a solvent. The intermolecular interactions are evaluated for interacting dimers. Here, a number of stacking geometries is tested, and dimers with mutual orientation of the molecules corresponding to the minimal binding energies are determined. The predicted charge carrier mobilities for stacks having minimal binding energies corroborate experimentally measured values. We conclude that DFT prediction of such stacks is a promising and computationally inexpensive approach to a rough estimation of transport properties. Additionally, the super‐cell of the experimentally resolved crystal structure is used to study the dynamics and to compute the charge transport along the hopping pathways. We discuss obtained high mobilities and relate them to the symmetry of DPP core. © 2018 Wiley Periodicals, Inc.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

A comparative analysis of symmetric diketopyrrolopyrrole‐cored small conjugated molecules with aromatic flanks: From geometry to charge transport

et al. 2018

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“…This is usually referred to as the heteroatom effect. In the case of molecules with substituents being five-membered aromatic monocycles with a single group 16 heteroatom (furan, thiophene, selenophene, tellurophene), it is known that the heteroatom effect is responsible for changes in their properties that respond to many demands relevant to organic synthesis [ 5 – 7 ], optics [ 8 – 10 ], electronics [ 11 ], material science [ 12 ], pharmacology [ 13 ] and biology [ 14 ]. If such molecules are in solution, the surrounding solvent usually exerts an additional influence on their properties.…”

Section: Introductionmentioning

confidence: 99%

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Matczak

Domagała

2017

J Mol Model

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In this work several molecular properties of symmetrically disubstituted formaldehyde and thioformaldehyde have been studied using a quantum chemistry approach based on density functional theory. Five-membered heteroaromatic rings containing a single group 16 heteroatom were taken into account as the substituents (i.e., furan-2-yl, thiophen-2-yl, selenophen-2-yl, tellurophen-2-yl, and the experimentally as yet unknown polonophen-2-yl). For the resulting ten formaldehyde and thioformaldehyde derivatives, the geometry, energetics, frontier molecular orbitals, dipole moment and polarizability of their molecules were examined in order to establish the effect of ring heteroatom on these properties. Furthermore, these properties were also determined for the molecules in three solvents of low polarity (benzene, chloroform, and dichloromethane) in order to expand our study to include solvent effects. The dipole moment and polarizability of the investigated molecules show regular variations when the ring heteroatom descends through group 16 and the solvent polarity grows. The heteroatom and/or solvent effects on the part of the studied properties are, however, more complex. An attempt is made to rationalize the observed variations in the molecular properties. The conformational behavior of the investigated molecules was also explored and the conformationally weighted values of dipole moment and polarizability are presented. Graphical abstractSome molecular properties of symmetrically disubstituted formaldehyde and thioformaldehyde Electronic supplementary materialThe online version of this article (doi:10.1007/s00894-017-3435-4) contains supplementary material, which is available to authorized users.

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“…However, P3 and P4 showed a considerably small magnitude of net dipole moments of ≈0.73 D. The calculated dihedral angles between the DTP units and their adjacent counterparts also exhibited distinguishable features (Figure 3b–e). P1 and P2 showed smaller values (0.01°–0.59° and 0.07°–0.48°, respectively) than P3 and P4 (0.35°–1.46° and 0.09°–1.02°) due to the expected intramolecular noncovalent NS and HF interactions [6a,17] . P1 and P2 achieved planar‐backbone conformations that are more favorable for intermolecular ππ stacking and better charge transport than P3 and P4 [15a] .…”

Section: Resultsmentioning

confidence: 95%

Thermally Stable and High‐Mobility Dithienopyran‐Based Copolymers: How Donor–Acceptor‐ and Donor–Donor‐Type Structures Differ in Thin‐Film Transistors

et al. 2021

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Although rapid and remarkable progress has been made in semiconducting polymers used in organic field‐effect transistors (OFETs), the development of novel π‐conjugated backbones remains the central issue in this field. High FET mobilities have been achieved for copolymers based on fused‐ring building blocks due to their strong tendency to form ππ stacks. However, introducing the recently formulated strong electron‐rich fused‐ring dithienopyran (DTP) unit in the polymer backbone has garnered considerably less attention. Herein, four new copolymers (donor–acceptor (DA)‐type versus donor–donor (DD)‐type structures) are synthesized based on the DTP unit by adopting different types of counterparts of the backbone. The characteristics of these copolymers, derived from different structural types, are investigated and compared and they are implemented in OFET devices. The DA‐type copolymers (P1 and P2) show higher charge‐carrier mobilities and better thermal stability than the DD‐type copolymers (P3 and P4), attributed to enhanced crystalline features induced by strong intermolecular interactions and preferential 3D‐textured molecular orientation of the DA‐type copolymers. Particularly, P1 exhibits the highest mobility of up to 0.22 cm2 V−1 s−1. This study provides a reference for understanding the influence of the backbone type on the structure–property relation and promotes the development of high‐performance DTP‐based copolymers.

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Conformational and electronic properties of small benzothiadiazole-cored oligomers with aryl flanking units: Thiophene versus Furan

Cited by 23 publications

References 55 publications

A comparative analysis of symmetric diketopyrrolopyrrole‐cored small conjugated molecules with aromatic flanks: From geometry to charge transport

A comparative analysis of symmetric diketopyrrolopyrrole‐cored small conjugated molecules with aromatic flanks: From geometry to charge transport

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Thermally Stable and High‐Mobility Dithienopyran‐Based Copolymers: How Donor–Acceptor‐ and Donor–Donor‐Type Structures Differ in Thin‐Film Transistors

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