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Highly Efficient Energy Transfer Cassettes by Assembly of Boronic Acid Derived Salicylidenehydrazone Complexes
Author(s) -
Santos Fábio M. F.,
Domínguez Zoe,
Alcaide María M.,
Matos Ana I.,
Florindo Helena F.,
Candeias Nuno R.,
Gois Pedro M. P.,
Pischel Uwe
Publication year - 2018
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201800150
Subject(s) - chromophore , bodipy , fluorescence , photochemistry , acceptor , conjugated system , chemistry , boronic acid , absorption (acoustics) , energy transfer , materials science , combinatorial chemistry , chemical physics , polymer , organic chemistry , optics , physics , composite material , condensed matter physics
Abstract Energy transfer cassettes that build on the platform of boronic acid derived salicylidenehydrazone (BASHY) complexes were prepared. The functional flexibility of the BASHY chromophore was underpinned by its tunable role as energy donor or acceptor, integrated in compact and non‐conjugated bichromophoric dyads. The energy transfer is highly efficient ( Φ ET >0.95) and is assumed to proceed mainly via a through‐bond mechanism. Both constituent chromophores benefit mutually from their integration in the cassettes: a) The pseudo Stokes shift is increased to 110–200 nm; b) the antenna (donor) chromophore improves the light absorption of the acceptor chromophore; and c) the emission window of the BASHY chromophore is expanded in the BASHY‐Bodipy dye without using strategies that compromise the observation of high quantum yields. The application of the cassettes for the formulation of fluorescent polymeric nanoparticles, that can be internalized in cells and observed by fluorescence imaging, was demonstrated using the BASHY‐Bodipy dye as an example.