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Circularly Polarized Luminescence of [6]Helicenes through Excited-State Intramolecular Proton Transfer


Göbel, Dominik; Míguez‐Lago, Sandra; Ruedas‐Rama, Maria Jose; Orte, Angel; Campaña, Araceli G; Juricek, Michal (2022). Circularly Polarized Luminescence of [6]Helicenes through Excited-State Intramolecular Proton Transfer. Helvetica Chimica Acta, 105(4):e202100221.

Abstract

We present the concept of combining circularly polarized luminescence (CPL) and excited-state intramolecular proton transfer (ESIPT) features into a single molecule as a strategy to generate high-performance ESIPT-based CPL materials. For this purpose, a [6]helicene bearing two ESIPT structural units was synthesized using a double Suzuki–Miyaura reaction and a double C(sp2)−H hydroxylation approach. The photophysical properties of the doubly hydroxylated [6]helicene were studied in parallel with a non-hydroxylated [6]helicene control compound, revealing that the presence of a chiral [6]helicene unit results in a strong CPL response and the presence of the ESIPT units in a considerable red shift. The red-shifted emission along with the outstanding glum (≈10−2) and a large Stokes shift makes the doubly hydroxylated [6]helicene a promising candidate for use in optoelectronics.

Abstract

We present the concept of combining circularly polarized luminescence (CPL) and excited-state intramolecular proton transfer (ESIPT) features into a single molecule as a strategy to generate high-performance ESIPT-based CPL materials. For this purpose, a [6]helicene bearing two ESIPT structural units was synthesized using a double Suzuki–Miyaura reaction and a double C(sp2)−H hydroxylation approach. The photophysical properties of the doubly hydroxylated [6]helicene were studied in parallel with a non-hydroxylated [6]helicene control compound, revealing that the presence of a chiral [6]helicene unit results in a strong CPL response and the presence of the ESIPT units in a considerable red shift. The red-shifted emission along with the outstanding glum (≈10−2) and a large Stokes shift makes the doubly hydroxylated [6]helicene a promising candidate for use in optoelectronics.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry
Uncontrolled Keywords:Inorganic Chemistry, Organic Chemistry, Physical and Theoretical Chemistry, Drug Discovery, Biochemistry, Catalysis
Language:English
Date:1 April 2022
Deposited On:10 Jan 2023 14:17
Last Modified:27 Feb 2024 02:55
Publisher:Wiley Open Access
ISSN:1522-2675
OA Status:Hybrid
Free access at:Publisher DOI. An embargo period may apply.
Publisher DOI:https://doi.org/10.1002/hlca.202100221
Project Information:
  • : FunderDeutscher Akademischer Austauschdienst
  • : Grant ID
  • : Project Title
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)