Understanding the properties of dithienylethenes functionalized for supramolecular self-assembly: a molecular modeling study

文献情報

出版日 2020-03-09

DOI 10.1039/C9CP06590C

インパクトファクター 3.676

著者

Laura Le Bras, Roxanne Berthin, Ismaïl Hamdi, Maroua Louati, Stéphane Aloïse, Michinori Takeshita

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要旨

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.

掲載誌

Physical Chemistry Chemical Physics

CiteScore: 5.5

自己引用率: 10.3%

年間論文数: 3036

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