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Synthesis and photophysical properties of a bichromophoric system hosting a disaccharide spacer

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Abstract

The synthesis of an efficient energy donor–acceptor system is reported, together with its photophysical properties. The bichromophoric species has been conceived to show potentialities for biological applications since a biocompatible disaccharide spacer, constituted of D-galactose and D-glucose derivatives, was used in compound 12 to connect two BODIPY units with different absorption/emission properties. The luminescence spectrum in acetonitrile of 12 shows an intense fluorescence band with a maximum at about 770 nm that is almost identical to that of the lowest-energy BODIPY, regardless of the excitation wavelength used. The quantum yield is 0.2 with an excited state lifetime of 2.5 ns. Excitation and ultrafast transient absorption spectroscopy demonstrates that a very efficient energy transfer takes place in 12 from the highest-energy lying BODIPY subunit to the lowest-energy emissive BODIPY moiety, with a time constant of about 31 ps. Noteworthily, the emission of 12 falls in the near infrared window, suitable for potential biological applications.

Graphical abstract: Synthesis and photophysical properties of a bichromophoric system hosting a disaccharide spacer

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Publication details

The article was received on 18 Jul 2017, accepted on 12 Sep 2017 and first published on 12 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB01764B
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis and photophysical properties of a bichromophoric system hosting a disaccharide spacer

    T. Papalia, A. Barattucci, S. Campagna, F. Puntoriero, T. Salerno and P. Bonaccorsi, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB01764B

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