1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization

1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and tris(THAO)-TT, were synthesized by Diels-Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality....

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Bibliographic Details
Published in:Synthetic communications 2024-08, Vol.54 (15), p.1263-1272
Main Authors: Hyun, Chang-Seok, Eo, Joohwan, Kwon, Ji Eon, An, Byeong-Kwan
Format: Article
Language:English
Subjects:
Anthracene
Benzoquinone
Chemical synthesis
Diels-Alder reactions
homoconjugation
Optical properties
Structural analysis
Thermal stability
through-space charge-transfer
Triptycene
triptycene trisquinone
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Summary:1,4,5,8-tetrasubstituted dihyroanthracene-based triptycene trisquinones (TT) molecules, THAO-TT and tris(THAO)-TT, were synthesized by Diels-Alder reaction between TT and 1,4,5,8-tetrakis(hexyloxy)anthracene to produce the extended triptycene derivatives containing electron-accepting functionality. The prepared THOA-TT and tris(THOA)-TT exhibited excellent thermal stability owing to the rigid TT framework. The optical and redox properties of THOA-TT and tris(THOA)-TT were controlled by the homoconjugation between the benzoquinone units and the peripheral units through the connecting methine groups.
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2024.2381074