Two new inherently chiral oligothiophenes characterized by the atropisomeric 3,3'-bithianaphtene scaffold functionalized with fused ring bithiophene derivatives, namely 4H-cyclopenta[2,1-b3:4b']dithiophene (CPDT) and dithieno[3,3-b:2',3'-d]pyrrole (DTP), were synthesized. The racemates were fully characterized and resolved into antipodes by enantioselective HPLC. The enantiomers were analyzed through different chiroptical techniques: electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) were employed to attribute the absolute configuration (AC). Comparison of experimental and calculated VCD spectra confirmed the DFT calculated conformational characteristics. The compound functionalized with two CPDT units was oxidized with FeCl3 , and ECD and CPL of the resulting material were measured. Circularly polarized luminescence (CPL) was measured to verify if inherently chiral oligothiophenes could be promising systems for chiral photonics applications.

Searching for Models Exhibiting High Circularly Polarized Luminescence : Electroactive Inherently Chiral Oligothiophenes / T. Benincori, G. Appoloni, P.R. Mussini, S. Arnaboldi, R. Cirilli, E. Quartapelle Procopio, M. Panigati, S. Abbate, G. Mazzeo, G. Longhi. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 24:43(2018 Aug 01), pp. 11082-11093. [10.1002/chem.201801158]

Searching for Models Exhibiting High Circularly Polarized Luminescence : Electroactive Inherently Chiral Oligothiophenes

G. Appoloni;P.R. Mussini;S. Arnaboldi;E. Quartapelle Procopio;M. Panigati;
2018

Abstract

Two new inherently chiral oligothiophenes characterized by the atropisomeric 3,3'-bithianaphtene scaffold functionalized with fused ring bithiophene derivatives, namely 4H-cyclopenta[2,1-b3:4b']dithiophene (CPDT) and dithieno[3,3-b:2',3'-d]pyrrole (DTP), were synthesized. The racemates were fully characterized and resolved into antipodes by enantioselective HPLC. The enantiomers were analyzed through different chiroptical techniques: electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) were employed to attribute the absolute configuration (AC). Comparison of experimental and calculated VCD spectra confirmed the DFT calculated conformational characteristics. The compound functionalized with two CPDT units was oxidized with FeCl3 , and ECD and CPL of the resulting material were measured. Circularly polarized luminescence (CPL) was measured to verify if inherently chiral oligothiophenes could be promising systems for chiral photonics applications.
circularly polarized luminescence (CPL); density functional calculations; electronic circular dichroism (ECD); inherent chirality; vibrational circular dichroism (VCD)
Settore CHIM/02 - Chimica Fisica
Settore FIS/02 - Fisica Teorica, Modelli e Metodi Matematici
Settore CHIM/06 - Chimica Organica
Enhancing VINCE (Versatile INherently Chiral Electrochemistry)
Laboratorio multifunzionale e centro di formazione per la caratterizzazione e la sperimentazione preapplicativa di smart materials
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/584730
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