Thermal reductive disproportionation of 3,3′,5,5′-tetraphenyldiphenoquinone with drastic color change: Potential prototype of data storage advanced materials

Md Awlad Hossain, Kazuhiko Akiyama, Kenta Goto, Ken Ichi Sugiura

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The solid-state thermal reaction of brilliant red 3,3′,5,5′-tetraphenyldiphenoquinone 1 was examined. Three reductive colorless products, the corresponding hydroquinone and two benzofuran derivatives, were formed at 289.5 °C. Theoretical studies indicated that thermally excited triplet species having radical-type oxygen atoms participated in the reaction. Single-crystal diffraction study revealed short atomic contacts between carbonyl oxygen and the ortho-positions of the phenyl group, and these short atomic contacts would promote the thermal solid-state reaction. The reductive reactions observed in cumene, a radical propagation solvent and/or a hydrogen radical donating solvent, supported our speculation.

Original languageEnglish
Pages (from-to)3784-3790
Number of pages7
JournalChemistrySelect
Volume1
Issue number13
DOIs
Publication statusPublished - Jan 1 2016

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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