Chakraborty, Saptarshi ; Varghese, Shinto ; Ghosh, Suhrit (2019) Supramolecular Nanowires from an Acceptor–Donor–Acceptor Conjugated Chromophore Chemistry – A European Journal, 25 (72). pp. 16725-16731. ISSN 0947-6539
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Official URL: http://doi.org/10.1002/chem.201904463
Related URL: http://dx.doi.org/10.1002/chem.201904463
Abstract
Oligothiophene derivatives have been extensively studied as p-type semiconducting materials in organic electronics applications. This work reports the synthesis, self-assembly and photophysical properties of acceptor–donor–acceptor (A–D–A)-type oligothiophene derivatives by end-group engineering of quaterthiophene (QT) with naphthalene monoimide (NMI) chromophores that are further connected to a trialkoxy benzamide wedge. Conjugation to the NMI units reduces the HOMO–LUMO gap significantly, and consequently the absorption spectrum exhibits a bathochromic shift of about 50 nm compared with QT. Furthermore, extended H-bonding interactions among the amido groups of the peripheral wedges produce entangled fibrillar nanostructures and gelation in hydrocarbon solvents such as methylcyclohexane, wherein the A–D–A chromophore exhibits typical H-aggregation. On the contrary, the fact that the same chromophore, lacking only the amido units, does not produce gels or H-aggregates indicates strong impact of H-bonding on the self-assembly. Computational studies revealed the electronic properties of the chromophore and predicted the geometry of a dimer in the H-aggregate that reasonably matches with the experimental results. Bulk electrical conductivity measurements determined an excellent conductivity of 2.3×10−2 S cm−1 for the H-aggregated system (OT-1), which is two orders of magnitude higher than that of the same chromophore lacking the amido groups (OT-2).
Item Type: | Article |
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Source: | Copyright of this article belongs to John Wiley & Sons, Inc |
ID Code: | 126025 |
Deposited On: | 17 Oct 2022 11:28 |
Last Modified: | 17 Oct 2022 11:28 |
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