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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
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1,4,5,8-tetrasubstituted dihydroanthracene-based triptycene trisquinones: Synthesis, structural, and physicochemical characterization

Chang-Seok Hyuna Department of Chemistry, The Catholic University of Korea, Bucheon, Gyeonggi-do, KoreaView further author information
,
Joohwan Eob Functional Composite Materials Research Center, Institute of Advanced Composite Materials, Korea Institute of Science and Technology (KIST), Wanju-gun, Jeonbuk, Korea;c Department of Materials Science and Engineering, Seoul National University, Seoul, KoreaView further author information
,
Ji Eon Kwonb Functional Composite Materials Research Center, Institute of Advanced Composite Materials, Korea Institute of Science and Technology (KIST), Wanju-gun, Jeonbuk, Korea;d Department of JBNU-KIST Industry Academia Convergence Research, Jeonbuk National University, Jeonbuk, KoreaView further author information
&
Byeong-Kwan Ana Department of Chemistry, The Catholic University of Korea, Bucheon, Gyeonggi-do, KoreaCorrespondence[email protected]
View further author information
Received 02 May 2024, Published online: 25 Jul 2024
 
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Abstract

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.

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Funding

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2017R1D1A1B03035785) and the Catholic University of Korea, Research Fund, 2022 (M-2022-B0008-00140).

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