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Synthesis and Properties of Five Ring Fused Aromatic Compounds Based S,S-Dioxide Benzothiophene

Abstract

Asymmetrical five ring fused compounds based S,S-dioxide benzothiophene, 9,9-dioctylfluorene[2,3-b]benzo[d]thiophene-S,S-dioxide(BTOF) and N-(2-decyltetradecyl)carbazole[2,3-b]benzo[d]thiophene-S,S-dioxide (BTOCz), were synthesized and characterized. BTOF and BTOCz were readily soluble in common organic solvents and exhibited high thermal stability with the melting points (Tms) of 119 oC and 150 oC, and thermal decomposition temperatures (Tds) of 280 oC and 338 oC, respectively. The highest occupied molecular orbital energy levels (HOMOs), the lowest unoccupied molecular orbital energy levels (LUMOs) and the band gaps (Egs) of BTOF and BTOCz were -6.11, -2.66 and 3.45 eV, -5.86, -2.52 and 3.34 eV, respectively. The photoluminescence (PL) spectra of BTOF and BTOCz were peaked at 404 and 420 nm in film, and the photoluminescence quantum yields (QPLs) of were 30% and 10% in toluene solution, respectively. BTOF and BTOCz showed the strong intramolecular charge transfer (ICT) characters,the relative high QPLs and the deeper HOMO and LUMO levels compared with the compounds BTF and BTCz. Compared with the symmetrically seven ring fused compounds FBTO and CzBTO, the asymmetrically five ring fused compounds BTOF and BTOCz owned relatively shallow HOMO levels, which can facilitate the holes injection, and therefore, could be potential construction units in organic semiconductors.

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Publication details

The article was received on 07 Nov 2017, accepted on 08 Jan 2018 and first published on 09 Jan 2018


Article type: Paper
DOI: 10.1039/C7NJ04306F
Citation: New J. Chem., 2018, Accepted Manuscript
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    Synthesis and Properties of Five Ring Fused Aromatic Compounds Based S,S-Dioxide Benzothiophene

    W. Yang, Y. Zhang, F. Peng, R. He, L. Ying and Y. Cao, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C7NJ04306F

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