期刊
JOURNAL OF MATERIALS CHEMISTRY C
卷 10, 期 19, 页码 7717-7723出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2tc01324j
关键词
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资金
- Agence Nationale de la Recherche [ANR-16-CE07-0024]
- JSPS KAKENHI [19H02790, 20K21227, 21H05401]
- Inamori Foundation
- Iketani Science and Technology Foundation
- JSPS Core-to-Core Program [JPJSCCA20180005]
- Grants-in-Aid for Scientific Research [20K21227, 21H05401] Funding Source: KAKEN
A series of pi-conjugated diindenothienothiophene derivatives (DITTs) with an extended as-indacene core have been synthesized and their closed-shell configuration has been confirmed by X-ray structure analysis. The bond lengths of the diindenoacene diradicaloids show peculiarities, which are influenced by the annellation mode at the outer rings. These featured molecules have low energy band gap and high electron affinities, similar to their benzo-fused indeno[2,1-c]-fluorene counterparts. Analysis of molecule tropicity reveals that the central rings of DITTs have weak antiaromaticity and can be considered as quinoidal molecules bridged by two sulphur atoms. Furthermore, three out of four molecules exhibit ambipolar behavior with moderate mobilities in OFETs.
A set of pi-conjugated diindenothienothiophene derivatives (DITTs) which formally possess an extended as-indacene core with 16 pi-electrons has been synthesised and their closed-shell configuration has been confirmed by X-ray structure analysis. Bond lengths analysis provides insight into the peculiar bond lengths observed for diindenoacene diradicaloids. The annellation mode at the outer rings has a great impact on the tropicity, optoelectrochemical properties and molecular packing. The featured molecules exhibit low energy band gap with values up to 1.30 eV and have high electron affinities with LUMO energies up to 3.86 eV. Their optical properties are similar to those of benzo-fused indeno[2,1-c]-fluorene (BIFs) counterparts possessing formally the as-indacene core. Analysis of the molecule tropicity using NICS and ACID plot shows that the central rings of DITTs are weakly antiaromatic and should be regarded as quinoidal molecules bridged by two sulphur atoms. Three out of four molecules show ambipolar behavior in OFETs with moderate mobilities.
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