Bluish hydrochromic naphthalenediimide salt: Change of hydrogen-bond interactions as the new mechanism of vapochromism

Tappei Tanabe, Tetsu Sato, Kentaro Fuku, Kaiji Uchida, Tamon Yamauchi, Shinya Takaishi, Hiroaki Iguchi

Research output: Contribution to journalArticlepeer-review

Abstract

Naphthalenediimide (NDI) is generally a yellowish to reddish chromophore, which shows vapochromism by the alternation of charge-transfer (CT) interactions at the NDI core. On the contrary, we discovered that the deprotonation of N,N - dihydroxy-1,4,5,8-naphthalenetetracarboxdiimide (NDI-(OH)2) gave a bluish organic salt with a hydrochromic property, which has been rare in conventional NDI derivatives. On the basis of the structural analyses and the calculation, the origin of the hydrochromism can be explained by the change of hydrogenbond interaction between the anionic imide group and H2O molecules.

Original languageEnglish
Pages (from-to)1479-1482
Number of pages4
JournalChemistry Letters
Volume50
Issue number8
DOIs
Publication statusPublished - 2021 Aug

Keywords

  • Hydrogen bond
  • Naphthalenediimide
  • Vapochromism

ASJC Scopus subject areas

  • Chemistry(all)

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