Inherently Chiral Macrocyclic Oligothiophenes: Easily Accessible Electrosensitive Cavities with Outstanding Enantioselection Performances |
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Authors: | Prof. Francesco Sannicolò Prof. Patrizia R. Mussini Prof. Tiziana Benincori Dr. Roberto Cirilli Prof. Sergio Abbate Serena Arnaboldi Simone Casolo Dr. Ettore Castiglioni Prof. Giovanna Longhi Dr. Rocco Martinazzo Dr. Monica Panigati Dr. Marco Pappini Dr. Elsa Quartapelle Procopio Dr. Simona Rizzo |
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Affiliation: | 1. Dipartimento di Chimica and C.I.Ma.I.Na, Università degli Studi di Milano, via Golgi 19, 20133 Milano (Italy);2. Dipartimento di Scienza e Alta Tecnologia, Università degli Studi dell'Insubria, via Valleggio 11, 22100 Como (Italy);3. Dipartimento del Farmaco, Istituto Superiore di Sanità viale Regina Elena 299, 00161 Roma (Italy);4. Dipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, viale Europa 11, 25123 Brescia (Italy);5. Centro Interdipartimentale Grandi Apparecchiature, Università degli Studi di Milano, via Golgi 19, 20133 Milano (Italy);6. Istituto di Scienze e Tecnologie Molecolari, Consiglio Nazionale delle Ricerche, via Golgi 19, 20133 Milano (Italy) |
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Abstract: | Linear conjugated oligothiophenes of variable length and different substitution pattern are ubiquitous in technologically advanced optoelectronic devices, though limitations in application derive from insolubility, scarce processability and chain‐end effects. This study describes an easy access to chiral cyclic oligothiophenes constituted by 12 and 18 fully conjugated thiophene units. Chemical oxidation of an “inherently chiral” sexithiophene monomer, synthesized in two steps from commercially available materials, induces the formation of an elliptical dimer and a triangular trimer endowed with electrosensitive cavities of different tunable sizes. Combination of chirality with electroactivity makes these molecules unique in the current oligothiophenes literature. These macrocycles, which are stable and soluble in most organic solvents, show outstanding chiroptical properties, high circularly polarized luminescence effects and an exceptional enantiorecognition ability. |
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Keywords: | chirality circularly polarized luminescence enantioselectivity macrocycles oligothiophenes |
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