Unravelling the ultrafast dynamics of a N-BODIPY compound

Year: 2022

Authors: Doria S.; Taddei M.; Cupellini L.; Biagiotti G.; Bartolini P.; Bussotti L.; Cicchi S.; Foggi P.; Mennucci B.; Di Donato M.

Autors Affiliation: ICCOM CNR, Via Madonna Piano 10, I-50019 Florence, FI, Italy; LENS European Lab Nonlinear Spect, Via N Carrara 1, I-50019 Florence, Italy; Univ Firenze, Dipartimento Chim Ugo Schiff, Via Lastruccia 3-13, I-50019 Florence, Italy; Univ Pisa, Dipartimento Chim & Chim Ind, Via G Moruzzi 13, I-56124 Pisa, Italy; Univ Perugia, Ctr Eccellenza Mat Innovat Nanostrutturati CEMIN, Dept Chem Biol & Biotechnol, Via Elce Sotto 8, I-06123 Perugia, Italy; INO CNR, Largo Fermi 6, I-50125 Florence, Italy.

Abstract: Although the photophysics of BODIPY compounds has been widely investigated in the last few years, their analogues N-BODIPY, with nitrogen substitution at the boron center, did not receive comparable attention. In this work we report the synthesis and photochemical characterization of a substituted N-BODIPY compound, by means of a combined theoretical and spectroscopic approach. Compared to a standard BODIPY, the compound under investigation presents a lower fluorescence quantum yield (QY) in the visible region. The excited state relaxation dynamics of the dye was studied in different solvents, showing further fluorescence quenching in polar solvents, and excited state decay rates strongly dependent on the environment polarity. The role of the pendant moieties and the involvement of charge transfer states in the excited state dynamics was experimentally addressed by transient absorption spectroscopy, and further analyzed with TD-DFT calculations, which allowed precise assignment of the transient signals to the correspondent electronic configuration. The complete picture of the N-BODIPY behavior shows the presence of both charge transfer and localized states, influencing the observed photophysics to different amounts, depending on the excitation conditions and the surrounding environment.

Journal/Review: DYES AND PIGMENTS

Volume: 200      Pages from: 110181-1  to: 110181-8

More Information: The authors thank the European Union´s Horizon 2020 research and innovation program under grant agreement n. 871124 Laserlab-Europe.
The authors also thank Dr Lorenzo Zani, Dr Massimo Calamnte and Dr Alessio Dessi from ICCOM-CNR in Sesto Fiorentino (FI), for support in the quantum yield measurements.
LC thanks the funding by the European Research Council, under the grant ERC-AdG-786714 (LIFETimeS).
KeyWords: Charge transfer states; DFT computations; N-BODIPY; Transient absorption spectroscopy; PHOTOINDUCED ELECTRON-TRANSFERENERGY-TRANSFERFLUORESCENT SENSORSCHARGE-TRANSFEREXCITED-STATESBORON-DIPYRRINDYE-LASERSDESIGNVERSATILECHEMISTRY
DOI: 10.1016/j.dyepig.2022.110181

Citations: 3
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