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Design,Synthesis and Characterization of a Visible-Light-Sensitive Molecular Switch and Its PEGylation Towards a Self-Assembling Molecule
Authors:Dr. Marco Paolino  Dr. Mario Saletti  Dr. Annalisa Reale  Prof. Mariano Licciardi  Dr. Paola Varvarà  Dr. Arnaud Marquette  Dr. Jérémie Léonard  Dr. Claudia Bonechi  Prof. Alessandro Donati  Prof. Gianluca Giorgi  Dr. Germano Giuliani  Prof. Benedetta Carlotti  Prof. Fausto Ortica  Prof. Loredana Latterini  Dr. Mariangela Gentile  Dr. Eugenio Paccagnini  Prof. Massimo Olivucci  Prof. Andrea Cappelli
Affiliation:1. Dipartimento di Biotecnologie, Chimica e Farmacia (Dipartimento di Eccellenza 2018–2022), Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy;2. Dipartimento di Scienze e Tecnologie Biologiche, Chimiche e Farmaceutiche (STEBICEF), Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy;3. Institut de Physique et Chimie des Matériaux de Strasbourg, Université de Strasbourg, CNRS UMR, 7504 Strasbourg, France;4. Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto, 8, 06123 Perugia, Italy;5. Dipartimento di Scienze della Vita, Università degli Studi di Siena, Via A. Moro, 53100 Siena, Italy;6. Dipartimento di Biotecnologie, Chimica e Farmacia (Dipartimento di Eccellenza 2018–2022), Università degli Studi di Siena, Via A. Moro 2, 53100 Siena, Italy

Chemistry Department, Bowling Green State University, 43403 Bowling Green, OH, USA) ok

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.
Keywords:HBDI-like chromophores  light-driven molecular switches  light-sensitive molecules  nanoaggregates  photoswitches  self-assembling molecules
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