Circularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores

Am. Chem. Soc., 2014, 136(9), pp 3346–3349.

Esther M. Sánchez-Carnerero †, Florencio Moreno†, Beatriz L. Maroto †, Antonia R. Agarrabeitia †,María J. Ortiz †, Bryan G. Vo ‡, Gilles Muller ‡, andSantiago de la Moya *†

^† Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040, Madrid, Spain and

^‡ Department of Chemistry, San José State University, San José, California 95192-0101, United States

 

Abstract

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.

 

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