HBDI-like chromophores represent a novel set of biomimetic switches mimicking the fluorophore of the green fluorescent protein that are currently studied with the hope to expand the molecular switch/motor toolbox. However, until now members capable of absorbing visible light in their neutral (i. e. non-anionic) form have not been reported. In this contribution we report the preparation of an HBDI-like chromophore based on a 3-phenylbenzofulvene scaffold capable of absorbing blue light and photoisomerizing on the picosecond timescale. More specifically, we show that double-bond photoisomerization occurs in both the E-to-Z and Z-to-E directions and that these can be controlled by irradiating with blue and UV light, respectively. Finally, as a preliminary applicative result, we report the incorporation of the chromophore in an amphiphilic molecule and demonstrate the formation of a visible-light-sensitive nanoaggregated state in water.

Paolino, M., Saletti, M., Reale, A., Licciardi, M., Varvarà, P., Marquette, A., et al. (2022). Design, Synthesis and Characterization of a Visible-Light-Sensitive Molecular Switch and Its PEGylation Towards a Self-Assembling Molecule. CHEMISTRY-A EUROPEAN JOURNAL, 28(50), e202201477-e202201477 [10.1002/chem.202201477].

Design, Synthesis and Characterization of a Visible-Light-Sensitive Molecular Switch and Its PEGylation Towards a Self-Assembling Molecule

Paolino, Marco
;
Saletti, Mario;Reale, Annalisa;Licciardi, Mariano;Bonechi, Claudia;Donati, Alessandro;Giorgi, Gianluca;Giuliani, Germano;Carlotti, Benedetta;Gentile, Mariangela;Paccagnini, Eugenio;Olivucci, Massimo;Cappelli, Andrea
2022-01-01

Abstract

HBDI-like chromophores represent a novel set of biomimetic switches mimicking the fluorophore of the green fluorescent protein that are currently studied with the hope to expand the molecular switch/motor toolbox. However, until now members capable of absorbing visible light in their neutral (i. e. non-anionic) form have not been reported. In this contribution we report the preparation of an HBDI-like chromophore based on a 3-phenylbenzofulvene scaffold capable of absorbing blue light and photoisomerizing on the picosecond timescale. More specifically, we show that double-bond photoisomerization occurs in both the E-to-Z and Z-to-E directions and that these can be controlled by irradiating with blue and UV light, respectively. Finally, as a preliminary applicative result, we report the incorporation of the chromophore in an amphiphilic molecule and demonstrate the formation of a visible-light-sensitive nanoaggregated state in water.
Paolino, M., Saletti, M., Reale, A., Licciardi, M., Varvarà, P., Marquette, A., et al. (2022). Design, Synthesis and Characterization of a Visible-Light-Sensitive Molecular Switch and Its PEGylation Towards a Self-Assembling Molecule. CHEMISTRY-A EUROPEAN JOURNAL, 28(50), e202201477-e202201477 [10.1002/chem.202201477].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/1215595
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