Open AccessCircularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores
Author(s) -
Esther M. SánchezCarnerero,
Florencio Moreno,
Beatriz Lora Maroto,
Antonia R. Agarrabeitia,
María J. Ortiz,
Bryan G. Vo,
Gilles Muller,
Santiago de la Moya Cerero
Publication year - 2014
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/ja412294s
Subject(s) - chromophore , chemistry , luminescence , moiety , photochemistry , absorption (acoustics) , molecule , stereochemistry , optoelectronics , organic chemistry , materials science , composite material
Circularly polarized luminescence (CPL) in simple (small, nonaggregated, nonpolymeric) O-BODIPYs (R)-1 and (S)-1 by irradiation with visible light is first detected as proof of the ability of a new structural design to achieve CPL from inherently achiral monochromophore systems in simple organic molecules. The measured level of CPL (|g(lum)|) in solution falls into the usual range of that obtained from other simple organic molecules (10(-5)-10(-2) range), but the latter having more complex architectures since axially chiral chromophores or multichromophore systems are usually required. The new design is based on chirally perturbing the acting achiral chromophore by orthogonally tethering a single axially chiral 1,1'-binaphtyl moiety to it. The latter does not participate as a chromophore in the light-absorption/emission phenomenon. This simple design opens up new perspectives for the future development of new small-sized CPL organic dyes (e.g., those based on other highly luminescent achiral chromophores and/or chirally perturbing moieties), as well as for the improvement of the CPL properties of the organic molecules spanning their use in photonic applications.