Issue 32, 2023

Columnar liquid-crystalline J-aggregates based on N-core-substituted naphthalene diimides

Abstract

We report two distinct approaches to prepare unprecedented liquid-crystalline (LC) J-aggregates based on bis-core-dendronized naphthalene diimides (NDIs). The NDI 1, with free imidic NH groups, spontanously self-assembles via hydrogen bonds into a columnar LC structure where the chromophores organize with the cores parallel to the columnar axis. Quantum mechanics calculations (GFN2-xTB method) and middle angle X-ray scattering confirmed the uncommon columnar architecture for the LC 1 which enable strong J-type exciton coupling between NDI cores. On the other hand, the NDI 2, with N-butyl groups at the imide positions, spontaneously self-assembles by cofacial π–π stacking into columnar H-aggregates; however mechanical shearing of the samples induces the reversible formation of weakly coupled J-aggregates. Surprisingly, this mechanochromic behavior is induced by a molecular reorganization of the NDI cores, which is accompanied by a fluorescence turn on. Thus, in this work we successfully applied two approaches to prepare for the first time LC NDI J-aggregates, which are highly appreciated materials for photonic applications.

Graphical abstract: Columnar liquid-crystalline J-aggregates based on N-core-substituted naphthalene diimides

Supplementary files

Article information

Article type
Paper
Submitted
04 5月 2023
Accepted
01 6月 2023
First published
06 6月 2023
This article is Open Access
Creative Commons BY-NC license

J. Mater. Chem. C, 2023,11, 10884-10892

Columnar liquid-crystalline J-aggregates based on N-core-substituted naphthalene diimides

E. Castellanos, R. M. Gomila, R. Manha, G. Fernández, A. Frontera and B. Soberats, J. Mater. Chem. C, 2023, 11, 10884 DOI: 10.1039/D3TC01560B

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