Circularly Polarized Luminescence of [6]Helicenes through Excited‐State Intramolecular Proton Transfer. Issue 4 (22nd March 2022)

• Record Type: Journal Article
• Authors: Göbel, Dominik; Míguez‐Lago, Sandra; Ruedas‐Rama, Maria Jose; Orte, Angel; Campaña, Araceli G.; Juríček, Michal
• Is Part Of: Helvetica chimica acta. Volume 105:Issue 4(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-03-22
• Subjects: chirality -- circularly polarized luminescence -- excited-state intramolecular proton transfer -- helicene -- luminescence -- proton transfer; Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.202100221
• Languages: English
• ISSNs: 0018-019X

Abstract

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(sp 2 )−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 g lum (≈10 −2 ) and a large Stokes shift makes the doubly hydroxylated [6]helicene a promising candidate for use in optoelectronics. Abstract :