title: Inherently chiral macrocyclic oligothiophenes: easily accessible electrosensitive cavities with outstanding enantioselection performances.
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.
authors.affiliation: Dipartimento di Chimica and C.I.Ma.I.Na, Università degli Studi di Milano, via Golgi 19, 20133 Milano (Italy). francesco.sannicolo@unimi.it.
authors.forename: Francesco
authors.initials: F
authors.lastname: Sannicolò
authors.forename: Patrizia R
authors.initials: PR
authors.lastname: Mussini
authors.forename: Tiziana
authors.initials: T
authors.lastname: Benincori
authors.forename: Roberto
authors.initials: R
authors.lastname: Cirilli
authors.forename: Sergio
authors.initials: S
authors.lastname: Abbate
authors.forename: Serena
authors.initials: S
authors.lastname: Arnaboldi
authors.forename: Simone
authors.initials: S
authors.lastname: Casolo
authors.forename: Ettore
authors.initials: E
authors.lastname: Castiglioni
authors.forename: Giovanna
authors.initials: G
authors.lastname: Longhi
authors.forename: Rocco
authors.initials: R
authors.lastname: Martinazzo
authors.forename: Monica
authors.initials: M
authors.lastname: Panigati
authors.forename: Marco
authors.initials: M
authors.lastname: Pappini
authors.forename: Elsa
authors.initials: E
authors.lastname: Quartapelle Procopio
authors.forename: Simona
authors.initials: S
authors.lastname: Rizzo
mesh_terms: D002712:Chlorides / Q000737:chemistry; D002942:Circular Dichroism; D055664:Electrochemical Techniques; D005290:Ferric Compounds / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012997:Solvents / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013876:Thiophenes / Q000737:chemistry*
chemical_list: D002712:Chlorides; D005290:Ferric Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; D012997:Solvents; D013876:Thiophenes; C520246:sexithiophene; C024555:ferric chloride
keywords: chirality; circularly polarized luminescence; enantioselectivity; macrocycles; oligothiophenes