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

doi:10.1246/cl.210275

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

SCI - Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	1479-1482
Number of pages	4
Journal	Chemistry Letters
Volume	50
Issue number	8
DOIs	https://doi.org/10.1246/cl.210275
Publication status	Published - 2021 Aug

Keywords

Hydrogen bond
Naphthalenediimide
Vapochromism

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.210275

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

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.",

keywords = "Hydrogen bond, Naphthalenediimide, Vapochromism",

author = "Tappei Tanabe and Tetsu Sato and Kentaro Fuku and Kaiji Uchida and Tamon Yamauchi and Shinya Takaishi and Hiroaki Iguchi",

note = "Funding Information: This work was partly supported by JSPS KAKENHI Grant Numbers JP18K14233 (H.I.) and JP21H01901 (H.I.), by the Toyota Riken Scholar Program (H.I.), and by the Kato Foundation for Promotion of Science KJ-2916 (H.I.). Publisher Copyright: {\textcopyright} 2021 Chemical Society of Japan. All rights reserved.",

year = "2021",

month = aug,

doi = "10.1246/cl.210275",

language = "English",

volume = "50",

pages = "1479--1482",

journal = "Chemistry Letters",

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publisher = "Chemical Society of Japan",

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TY - JOUR

T1 - Bluish hydrochromic naphthalenediimide salt

T2 - Change of hydrogen-bond interactions as the new mechanism of vapochromism

AU - Tanabe, Tappei

AU - Sato, Tetsu

AU - Fuku, Kentaro

AU - Uchida, Kaiji

AU - Yamauchi, Tamon

AU - Takaishi, Shinya

AU - Iguchi, Hiroaki

N1 - Funding Information: This work was partly supported by JSPS KAKENHI Grant Numbers JP18K14233 (H.I.) and JP21H01901 (H.I.), by the Toyota Riken Scholar Program (H.I.), and by the Kato Foundation for Promotion of Science KJ-2916 (H.I.). Publisher Copyright: © 2021 Chemical Society of Japan. All rights reserved.

PY - 2021/8

Y1 - 2021/8

N2 - 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.

AB - 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.

KW - Hydrogen bond

KW - Naphthalenediimide

KW - Vapochromism

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DO - 10.1246/cl.210275

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EP - 1482

JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

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

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Keywords

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