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      Designing efficient photochromic dithienylethene dyads†

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      a , a , b ,
      Chemical Science
      Royal Society of Chemistry

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          Abstract

          The impact of chemical substitution on the optical properties of ca. 30 dithienylethene (DTE) dyads is investigated with first-principles approaches, with the aim to provide useful guidelines for obtaining more efficient DTE multimers.

          Abstract

          Aiming at designing more efficient multiphotochromes, we investigate with the help of ab initio tools the impact of the substitution on a series of dimers constituted of two dithienylethene (DTE) moieties, strongly coupled to each other through an ethynyl linker. The electronic structure and the optical properties of a large panel of compounds, substituted on different positions by various types of electroactive groups, have been compared with the aim of designing a dyad in which the three possible isomers (open–open, closed–open, closed–closed) can be reached. We show that appending the reactive carbons atoms of the DTE core with electroactive groups on one of the two photochromes allows cyclisation to be induced on a specific moiety, which leads to the formation of the desired closed–open isomer. Substituting the lateral positions of the thiophene rings provides further control of the topology of the frontier molecular orbitals, so that the electronic transition inducing the second ring closure stands out in the spectrum of the intermediate isomer.

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          Author and article information

          Journal
          Chem Sci
          Chem Sci
          Chemical Science
          Royal Society of Chemistry
          2041-6520
          2041-6539
          1 June 2015
          2 April 2015
          : 6
          : 6
          : 3495-3504
          Affiliations
          [a ] Chimie Et Interdisciplinarité, Synthèse, Analyse, Modélisation (CEISAM) , UMR CNRS no. 6230 , Université de Nantes , BP 92208, 2, Rue de la Houssinière , 44322 Nantes Cedex 3 , France . Email: denis.jacquemin@ 123456univ-nantes.fr
          [b ] Institut Universitaire de France , 103, blvd Saint-Michel , F-75005 Paris Cedex 05 , France
          Article
          c5sc00856e
          10.1039/c5sc00856e
          5659146
          40936dea-0598-4342-95e2-73aedb8a395e
          This journal is © The Royal Society of Chemistry 2015

          This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)

          Categories
          Chemistry

          Notes

          †Electronic supplementary information (ESI) available: Comparison between ADC(2) and CAM-B3LYP for a single DTE, conformational study of dyad 1 and basis set effect on the computed optical properties, TD-DFT results for a “normal-inverse” dimer. See DOI: 10.1039/c5sc00856e


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