期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 25, 期 72, 页码 16725-16731出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201904463
关键词
aggregation; conducting materials; gels; hydrogen bonds; supramolecular chemistry
资金
- CSIR
- DST [DST/SJF/CSA-01/2-14-15]
- Technical Research Centre, IACS [AI/1/62/IACS/2015]
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 2.3x10(-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).
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