Dataset Information

Circularly polarized luminescence by visible-light absorption in a chiral O-BODIPY dye: unprecedented design of CPL organic molecules from achiral chromophores.

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.

SUBMITTER: Sanchez-Carnerero EM

PROVIDER: S-EPMC3984031 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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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 EM Moreno Florencio F Maroto Beatriz L BL Agarrabeitia Antonia R AR Ortiz María J MJ Vo Bryan G BG Muller Gilles G de la Moya Santiago S

Journal of the American Chemical Society 20140221 9

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 archi ...[more]

PMID: 24524257

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Project description:Over the last decade, molecules capable of emitting circularly polarized light have attracted growing attention for potential technological and biological applications. The efficiency of such devices depend on multiple parameters, in particular the magnitude and wavelength of the peak of emitted light, and also on the dissymmetry factor for chiral applications. In light of these considerations, molecular systems with tunable optical properties, preferably in the visible spectral region, are particularly appealing. This is the case of boron dipyrromethene (BODIPY) dyes, which exhibit large molecular absorption coefficients, have high fluorescence yields, are very stable, both thermally and photochemically, and can be easily functionalized. The latter property has been extensively exploited in the literature to produce chromophores with a wide range of optical properties. Nevertheless, only a few chiral BODIPYs have been synthetized and investigated so far. Using a recently reported axially chiral BODIPY derivative where an axially chiral BINOL unit has been attached to the chromophore unit, we present a comprehensive computational protocol to predict and interpret the one-photon absorption and emission spectra, together with their chiroptical counterparts. From the physico-chemical properties of this molecule, it will be possible to understand the origin of the circularly polarized luminescence better, thus helping to fine-tune the properties of interest. The sensitivity of such processes require accurate results, which can be achieved through a proper account of the vibrational structure in optical spectra. Methodologies to compute vibrationally-resolved electronic spectra can now be applied on relatively large chromophores, such as BODIPYs, but require more extensive computational protocols. For this reason, particular attention is paid in the description of the different steps of the protocol, and the potential pitfalls. Finally, we show how, by means of appropriate tools and approaches, data from intermediate steps of the simulation of the final spectra can be used to obtain further insights into the properties of the molecular system under investigation and the origin of the visible bands.

Dataset Information

Circularly polarized luminescence by visible-light absorption in a chiral O-BODIPY dye: unprecedented design of CPL organic molecules from achiral chromophores.

Publications

Circularly polarized luminescence by visible-light absorption in a chiral O-BODIPY dye: unprecedented design of CPL organic molecules from achiral chromophores.

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