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Title

Design, synthesis and evaluation of multifunctional dithienothiophene monomers, dimers and trimers
Author
Macchione, Mariano
Director
Matile, Stefan
Defense Thèse de doctorat : Univ. Genève, 2018 - Sc. 5302 - 2018/12/20
Abstract Inspired by the color tuning of carotenoids pigments in lobster, our group highlighted how the interplay of chromophore polarization and planarization is the key point for the design of environment sensitive fluorescent probes, named “flippers”. They are constituted by an electron rich DTT (dithieno[3,2-b;20,30-d]thiophene) moiety connected through a  bond to an electron poor DTT-S,S-dioxide to achieve a fully operative push-pull system. A polar head group is linked to the hydrophobic core to ensure right orientation inside the lipid membrane. Sensitivity comes from the ability to adopt a twisted or planar conformation in response to the packing of the environment. The difference observed in excitation spectrum of the two conformation can be used to detect and study membrane tension. To screen the effect of further chemical modifications, chromophore length and oxidation, steric hindrance and extended conjugation are the main factors that can be evaluated in order to affect the spectroscopic properties of these powerful probes.
Keywords Flipper — Mechanosensitivity — Mechanophores — Trimers — Dimers — Dithienothiophene — Fluorescent probes — Chalcogen bonding.
Identifiers
URN: urn:nbn:ch:unige-1146125
Full text
Thesis (29.3 MB) - document accessible for UNIGE members only Limited access to UNIGE
Structures
Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
Research group Groupe Matile
Citation
(ISO format) 		MACCHIONE, Mariano. Design, synthesis and evaluation of multifunctional dithienothiophene monomers, dimers and trimers. Université de Genève. Thèse, 2018. https://archive-ouverte.unige.ch/unige:114612

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Deposited on : 2019-02-27

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