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      Fluorine as a robust balancer for tuning the reactivity of topo-photoreactions of chalcones and the photomechanical effects of molecular crystals

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          Abstract

          The higher the number of fluorine atoms, the higher the topological photo-induced [2 + 2] cycloaddition reactivity of chalcones.

          Abstract

          Fluorine-free chalcones and chalcones bearing different numbers of fluorine atoms have been synthesized. It is found that fluorine can tune the reactivity of photo-induced [2 + 2] cycloaddition reactions in crystals. The higher the number of fluorine atoms, the higher the reactivity of the photodimerization. The single crystal structures and Hirshfeld surface analysis illustrated that the introduction of fluorine not only increased the molecular planarity but could also steer the potentially reactive double bonds in appropriate positions of the crystal lattices to meet Schmidt's criteria. Therefore, the stereospecific [2 + 2] cycloaddition reactions took place to afford one diastereoisomer from the reactive chalcones except for ( E)-3-(4-fluorophenyl)-1-phenylprop-2-en-1-one ( 1FChH). Additionally, the chalcone-based molecular crystals exhibited various photomechanical behaviors, such as bending toward or away from the light source, swinging, cracking and jumping, driven by topo-photoreactions. As expected, the more efficient photo-induced [2 + 2] cycloaddition reactions in crystalline states led to more significant motions of the molecular crystals. Powder X-ray diffraction results suggested that the solid state [2 + 2] cycloaddition reactions changed the unit cell of the single crystals. The photo-induced bending toward or away from the light source for the needle-like crystals originated from the contraction or the expansion of the phototropic surface. Hence, the robust balancer fluorine in chalcones might play an important role in the crystalline packing. This provides a facile approach in crystal engineering to fabricate photo-induced mechanically responsive crystalline materials.

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          Most cited references76

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          Hirshfeld surface analysis

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            Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces

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              Photodimerization in the solid state

              G. Schmidt (1971)
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                Author and article information

                Contributors
                Journal
                CRECF4
                CrystEngComm
                CrystEngComm
                Royal Society of Chemistry (RSC)
                1466-8033
                September 01 2021
                2021
                : 23
                : 34
                : 5856-5868
                Affiliations
                [1 ]State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130021, P. R. China
                Article
                10.1039/D1CE00086A
                56e08291-0355-4fdd-837c-378e91215807
                © 2021

                http://rsc.li/journals-terms-of-use

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