Issue 7, 2024

Tunable mechanochromic luminescence of benzofuran-fused pyrazine: effects of alkyl chain length and branching pattern

Abstract

A series of bis(benzofuro)[2,3-b:2′,3′-e]pyrazines (BBFPz) with various alkyl chains of different length have been synthesized, and the effects of chain length on their mechanochromic luminescent properties were investigated. Some derivatives gave two polymorphs depending on the recrystallization conditions. Although the luminescent properties of the derivatives were almost the same in the solution state, distinct luminescence depending on their alkyl chains was observed in the crystalline state. The obtained crystals could be categorized into four packing motifs (Type A–D) with unique mechanochromic luminescent properties. Type D crystals with linear alkyl groups did not show mechanochromic luminescent characters. The luminescent color of Linear-Me slightly and reversibly changed upon grinding. Linear-Et (Form 1) and Linear-sBu, which belong to Type B and C, respectively, exhibited mechanochromic luminescent properties with rapid self-recovery character. The other crystals showed mechanochromic luminescent properties with relatively slow self-recovery rates. The present work demonstrates a quite limited example of covering both on/off mechanochromic luminescence (MCL) and self-recovery characters with a specific luminophore skeleton by changing the alkyl chains.

Graphical abstract: Tunable mechanochromic luminescence of benzofuran-fused pyrazine: effects of alkyl chain length and branching pattern

Supplementary files

Article information

Article type
Paper
Submitted
23 Dec 2023
Accepted
26 Jan 2024
First published
27 Jan 2024
This article is Open Access
Creative Commons BY license

J. Mater. Chem. C, 2024,12, 2370-2378

Tunable mechanochromic luminescence of benzofuran-fused pyrazine: effects of alkyl chain length and branching pattern

S. Nakamura, K. Okubo, Y. Nishii, K. Hirano, N. Tohnai and M. Miura, J. Mater. Chem. C, 2024, 12, 2370 DOI: 10.1039/D3TC04748B

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements