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Inherently Chiral Macrocyclic Oligothiophenes: Easily Accessible Electrosensitive Cavities with Outstanding Enantioselection Performances
Author(s) -
Sannicolò Francesco,
Mussini Patrizia R.,
Benincori Tiziana,
Cirilli Roberto,
Abbate Sergio,
Arnaboldi Serena,
Casolo Simone,
Castiglioni Ettore,
Longhi Giovanna,
Martinazzo Rocco,
Panigati Monica,
Pappini Marco,
Quartapelle Procopio Elsa,
Rizzo Simona
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201404331
Subject(s) - trimer , chirality (physics) , thiophene , dimer , monomer , conjugated system , materials science , molecule , luminescence , chemistry , polymer , combinatorial chemistry , photochemistry , organic chemistry , optoelectronics , chiral symmetry , physics , quantum mechanics , nambu–jona lasinio model , quark
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.