Highly Efficient Energy Transfer Cassettes by Assembly of Boronic Acid Derived Salicylidenehydrazone Complexes

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 (ΦET>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.The financial support of the Portuguese Fundac ̧a ̃o para a Cieˆnciae a Tecnologia (FCT) (grants SFRH/BD/94779/2013, PTDC/QEQ-QOR/1434/2014, PTDC/QEQ-MED/5512/2014, FEDER-029967,SAICTPAC/0019/2015, iMed.ULisboa grant UID/DTP/04138/2013,UTAP-ICDT/DTP-FTO/0016/2014, PhD fellowship PD/BD/113959/20for A.I.M), the Spanish Ministerio de Ciencia, Innovacio ́nyUniversidades (grants CTQ2014-54729-C2-1-P, CTQ2017-89832-Pand PhD fellowship BES-2015-074458 for Z.D.), the Junta deAndalucı ́a (P12-FQM-2140), the ERDF, and the Academy of Finland(decision 287954) is gratefully acknowledged. CSC–IT Center forScience Ltd, Finland is thanked for the allocation of computa-tional resource