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.

Inherently chiral macrocyclic oligothiophenes : easily accessible electrosensitive cavities with outstanding enantioselection performances / F. Sannicolò, P.R. Mussini, T. Benincori, R. Cirilli, S. Abbate, S. Arnaboldi, S. Casolo, E. Castiglioni, G. Longhi, R. Martinazzo, M. Panigati, M. Pappini, E.Q. Procopio, S. Rizzo. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 20:47(2014 Nov 17), pp. 15298-15302. [10.1002/chem.201404331]

Inherently chiral macrocyclic oligothiophenes : easily accessible electrosensitive cavities with outstanding enantioselection performances

F. Sannicolò
Primo
;
P.R. Mussini
Secondo
;
S. Arnaboldi;S. Casolo;R. Martinazzo;M. Panigati;M. Pappini;
2014

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.
Chirality; Circularly polarized luminescence; Enantioselectivity; Macrocycles; Oligothiophenes; Chemistry (all)
Settore CHIM/06 - Chimica Organica
17-nov-2014
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/249388
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