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

6 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

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Color
Data storage equipment
Solid state reactions
Hydrogen
Reactive Oxygen Species
Diffraction
Single crystals
Oxygen
Derivatives
Atoms
Hot Temperature
hydroquinone
benzofuran
cumene

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Thermal reductive disproportionation of 3,3′,5,5′-tetraphenyldiphenoquinone with drastic color change : Potential prototype of data storage advanced materials. / Hossain, Md Awlad; Akiyama, Kazuhiko; Goto, Kenta; Sugiura, Ken Ichi.

In: ChemistrySelect, Vol. 1, No. 13, 01.01.2016, p. 3784-3790.

Research output: Contribution to journalArticle

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