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

Tiziana Benincori, Giulio Appoloni, Patricia Romana Mussini, Serena Arnaboldi, Roberto Cirilli, Elsa Quartapelle Procopio, Monica Panigati, Sergio Abbate, Giuseppe Mazzeo, Giovanna Longhi

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)11082-11093
Number of pages12
JournalChemistry - A European Journal
Volume24
Issue number43
DOIs
Publication statusPublished - Aug 1 2018

    Fingerprint

Keywords

  • circularly polarized luminescence (CPL)
  • density functional calculations
  • electronic circular dichroism (ECD)
  • inherent chirality
  • vibrational circular dichroism (VCD)

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Benincori, T., Appoloni, G., Mussini, P. R., Arnaboldi, S., Cirilli, R., Quartapelle Procopio, E., Panigati, M., Abbate, S., Mazzeo, G., & Longhi, G. (2018). Searching for Models Exhibiting High Circularly Polarized Luminescence: Electroactive Inherently Chiral Oligothiophenes. Chemistry - A European Journal, 24(43), 11082-11093. https://doi.org/10.1002/chem.201801158