Mechanosensitive Oligodithienothiophenes: Transmembrane Anion Transport Along Chalcogen-Bonding Cascades

Article Article scientifique Article Mechanosensitive Oligodithienothiophenes: Transmembrane Anion Transport Along Chalcogen-Bonding Cascades eng 2018 author Macchione Mariano 829984 author Tsemperouli Maria 829578 author Goujon Antoine 858530 author Mallia Ajith 852993 author Sakai Naomi 131140 author Sugihara Kaori 818285 author Matile Stefan 129654 e1800014 10.1002/hlca.201800014 0018-019X The design, synthesis, and evaluation of multifunctional dithieno[3,2‐b;2′,3′‐d]thiophene (DTT) trimers is described. Twisted push‐push‐pull or donor‐donor‐acceptor (DDA) trimers composed of one DTT acceptor and two DTT donors show strong mechanochromism in lipid bilayer membranes. Red shifts in excitation rather than emission and fluorescence recovery with increasing membrane order are consistent with planarization of the twisted, extra‐long mechanophores in the ground state. The complementary pull‐pull‐pull or AAA trimers with deep σ holes all along the scaffold are not mechanochromic in membranes but excel with submicromolar anion transport activity. Anion transport along membrane‐spanning strings of chalcogen‐bond donors is unprecedented and completes previous results on transmembrane cascades that operate with equally unorthodox interactions such as halogen bonds and anion‐π interactions. Dewey 540 36 Département de chimie organique 141 38 Département de chimie physique 142 false 761 Groupe Matile 690 Groupe Sugihara Helvetica Chimica Acta 101 4 6a33d9cc-fca2-4e4b-8c92-7a3800d797be Article (Published version) Public Macchione_et_al-2018-Helvetica_Chimica_Acta.pdf 6862218 application/pdf CC BY-NC openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique Faculté des sciences / Section de chimie et biochimie / Département de chimie physique

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Mechanosensitive Oligodithienothiophenes: Transmembrane Anion Transport Along Chalcogen-Bonding Cascades	Helvetica Chimica Acta			2018	578	204

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Mallia, Ajith