| Title: |
Understanding the properties of dithienylethenes functionalized for supramolecular self-assembly: a molecular modeling study. |
| Authors: |
Le Bras, Laurine; Berthin, R.; Hamdi, Ismaïl; Louati, M.; Aloise, Stephane; Takeshita, M.; Adamo, Carlo; Perrier, Aurélie |
| Contributors: |
Université de Lille; CNRS; Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL ENSCP; Institute of Chemistry for Life and Health Sciences iCLeHS; Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement - UMR 8516 LASIRE; Laboratoire Avancé de Spectroscopie pour les Intéractions la Réactivité et l'Environnement (LASIRE) - UMR 8516; Institut Universitaire de France IUF |
| Publication Year: |
2024 |
| Collection: |
LillOA (Lille Open Archive - Université de Lille) |
| Description: |
A dithienylethene (DTE) photochromic compound functionalized by ureidopyrimidinone (UPy) quadruple hydrogen bonding blocks was synthesized by Takeshita and coworkers [Takeshita et al., Chem. Commun., 2005, 761] in order to form a light-responsive supramolecular self-assembling system. In solution, the formation of supramolecular assemblies was only observed for one DTE isomer, namely the closed-form isomer. To rationalize this experimental finding, with the help of Molecular Dynamics (MD) and (time-dependent) DFT calculations, the behaviour of open-form and closed-form monomers, dimers, hexamers and π-stacked dimers in solution is investigated. Our simulations show that, for the open-form oligomers, the progression of the supramolecular assembly is hindered due to (i) the possible formation of a very stable cyclic dimer for the open-form parallel isomer, (ii) the relative flexibility of the open-form oligomers compared to their closed-form counterparts, and (iii) the possible existence of π-stacked dimers that constitute bottlenecks blocking the progression of the supramolecular self-assembly. |
| Document Type: |
article in journal/newspaper |
| Language: |
English |
| Relation: |
Physical Chemistry Chemical Physics; Phys Chem Chem Phys; http://hdl.handle.net/20.500.12210/109564 |
| Availability: |
https://hdl.handle.net/20.500.12210/109564 |
| Rights: |
info:eu-repo/semantics/closedAccess |
| Accession Number: |
edsbas.8EA0C499 |
| Database: |
BASE |