Cargando…

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

[Image: see text] 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...

Descripción completa

Detalles Bibliográficos
Autores principales: Sánchez-Carnerero, Esther M., Moreno, Florencio, Maroto, Beatriz L., Agarrabeitia, Antonia R., Ortiz, María J., Vo, Bryan G., Muller, Gilles, Moya, Santiago de la
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3984031/
https://www.ncbi.nlm.nih.gov/pubmed/24524257
http://dx.doi.org/10.1021/ja412294s
_version_ 1782311387001782272
author Sánchez-Carnerero, Esther M.
Moreno, Florencio
Maroto, Beatriz L.
Agarrabeitia, Antonia R.
Ortiz, María J.
Vo, Bryan G.
Muller, Gilles
Moya, Santiago de la
author_facet Sánchez-Carnerero, Esther M.
Moreno, Florencio
Maroto, Beatriz L.
Agarrabeitia, Antonia R.
Ortiz, María J.
Vo, Bryan G.
Muller, Gilles
Moya, Santiago de la
author_sort Sánchez-Carnerero, Esther M.
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-3984031
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-39840312015-02-13 Circularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores Sánchez-Carnerero, Esther M. Moreno, Florencio Maroto, Beatriz L. Agarrabeitia, Antonia R. Ortiz, María J. Vo, Bryan G. Muller, Gilles Moya, Santiago de la J Am Chem Soc [Image: see text] 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. American Chemical Society 2014-02-13 2014-03-05 /pmc/articles/PMC3984031/ /pubmed/24524257 http://dx.doi.org/10.1021/ja412294s Text en Copyright © 2014 American Chemical Society
spellingShingle Sánchez-Carnerero, Esther M.
Moreno, Florencio
Maroto, Beatriz L.
Agarrabeitia, Antonia R.
Ortiz, María J.
Vo, Bryan G.
Muller, Gilles
Moya, Santiago de la
Circularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores
title Circularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores
title_full Circularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores
title_fullStr Circularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores
title_full_unstemmed Circularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores
title_short Circularly Polarized Luminescence by Visible-Light Absorption in a Chiral O-BODIPY Dye: Unprecedented Design of CPL Organic Molecules from Achiral Chromophores
title_sort circularly polarized luminescence by visible-light absorption in a chiral o-bodipy dye: unprecedented design of cpl organic molecules from achiral chromophores
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3984031/
https://www.ncbi.nlm.nih.gov/pubmed/24524257
http://dx.doi.org/10.1021/ja412294s
work_keys_str_mv AT sanchezcarnereroestherm circularlypolarizedluminescencebyvisiblelightabsorptioninachiralobodipydyeunprecedenteddesignofcplorganicmoleculesfromachiralchromophores
AT morenoflorencio circularlypolarizedluminescencebyvisiblelightabsorptioninachiralobodipydyeunprecedenteddesignofcplorganicmoleculesfromachiralchromophores
AT marotobeatrizl circularlypolarizedluminescencebyvisiblelightabsorptioninachiralobodipydyeunprecedenteddesignofcplorganicmoleculesfromachiralchromophores
AT agarrabeitiaantoniar circularlypolarizedluminescencebyvisiblelightabsorptioninachiralobodipydyeunprecedenteddesignofcplorganicmoleculesfromachiralchromophores
AT ortizmariaj circularlypolarizedluminescencebyvisiblelightabsorptioninachiralobodipydyeunprecedenteddesignofcplorganicmoleculesfromachiralchromophores
AT vobryang circularlypolarizedluminescencebyvisiblelightabsorptioninachiralobodipydyeunprecedenteddesignofcplorganicmoleculesfromachiralchromophores
AT mullergilles circularlypolarizedluminescencebyvisiblelightabsorptioninachiralobodipydyeunprecedenteddesignofcplorganicmoleculesfromachiralchromophores
AT moyasantiagodela circularlypolarizedluminescencebyvisiblelightabsorptioninachiralobodipydyeunprecedenteddesignofcplorganicmoleculesfromachiralchromophores