RT Journal Article
T1 Stimuli responsive behavior in a D–A–D organic fluorophore: the role of cold crystallization
A1 Afsar Uddin, Mohammad
A1 Gámez-Valenzuela, Sergio
A1 Ruiz-Delgado, María del Carmen
A1 Gómez-Lor, Berta
K1 Química física
AB Herein, dimethyl-4,7-di(2-thienyl)-2,1,3-benzothiadiazole-5,6-dicarboxylate (DTBTE) is introduced as a highly efficient fluorophore with multi-stimuli responsive properties. Its molecular structure, consisting of a benzothiadiazole (BTD) core functionalized with ester groups and thiophene rings, results in a highly flexible framework with dynamic conformational behavior and low rotational barriers. These characteristics allow DTBTE to exhibit cold crystallization at 80 1C, accompanied by a pronounced and reversible color change. This transition can be reversed, restoring the amorphous state via externalstimuli such as solvent fuming or mechanical shearing. Density functional theory (DFT) calculations, combined with advanced characterization techniques such as single-crystal X-ray analysis and IR and Raman spectroscopy, provide detailed insight into the mechanisms driving the phase transformations and their associated color changes. In particular, the flexibility of the ester groups plays a crucial role inenabling cold crystallization, as it facilitates the formation of a complex hydrogen bond network.Additionally, the switchable emission colours are attributed to cis/trans conformational changes in the thiophene groups during the transition between the crystalline and the amorphous phases. These findings highlight DTBTE as a promising platform for designing efficient stimuli-responsive materials and provide valuable guidelines for the development of new fluorophores exhibiting a dynamic behavior.
PB The Royal Society of Chemistry
YR 2025
FD 2025-04-26
LK https://hdl.handle.net/10630/41457
UL https://hdl.handle.net/10630/41457
LA eng
NO M. A. Uddin, S.Gámez-Valenzuela, M. C. Ruiz Delgado and B. Gomez-Lor, J. Stimuli responsive behavior in a D–A–D organic fluorophore: the role of cold crystallization. Mater. Chem. C, 2025, DOI:10.1039/D5TC00852B
NO MICINN
NO Junta de Andalucia
NO Universidad de Málaga
DS RIUMA. Repositorio Institucional de la Universidad de Málaga
RD 21 ene 2026