Journal
DYES AND PIGMENTS
Volume 187, Issue -, Pages -Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2021.109137
Keywords
Porphyrins; BODIPY; Triazine triads; Energy transfer
Funding
- University of Aveiro
- Instituto Superior Tecnico (IST, Portugal)
- FCT/MCTES (Fundacao para a Ciencia e Tecnologia/Ministerio da Ciencia e Tecnologia, Portugal)
- QOPNA [FCT UID/QUI/00062/2019]
- LAQVREQUIMTE [UIDB/50006/2020]
- CICECO-Aveiro Institute of Materials [UID/CTM/50011/2020, UID/CTM/50011/2019, UID/NAN/50024/2019]
- European Union
- FEDER
- QREN
- COMPETE within the PT2020 Partnership Agreement
- FCT [CEECIND/00553/2017]
- Fundacao de Amparo a Pesquisa do Estado do Rio de Janeiro-FAPERJ [101.125/2018, 211.119/2019, 201.754/2018]
- [UID/EMS/00481/2013]
- [PTDC/FISNAN/4662/2014]
- [PTDC/NAN-MAT/29317/2017]
- [PTDC/QUI-QFI/29319/2017]
- [LISBOA-01-0145-FEDER-029319]
- [UIDB/00100/2020]
- [IST-ID/95/2018]
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Two novel triads connecting a BODIPY to ethylenediamine substituted porphyrins via triazine linker have been synthesized, exhibiting extended absorption and efficient energy transfer properties. The nonlinear upconverted emission properties of the triads, featuring large two-photon absorption cross-section values, could be beneficial for sensing and imaging applications.
Two novel triads connecting a BODIPY to ethylenediamine substituted porphyrins via triazine linker have been synthesized and characterized. One of the triads is a linear D-A structure with one BODIPY (D) and one porphyrin (A) bridged by the triazine linker and the other one is a branched A-D 4 structure with the porphyrin core linked to four BODIPY units. The triads show extended absorption in the visible region with contributions from both porphyrin (Soret band centred at 410-430 nm) and BODIPY units (strong absorption at N 502 nm) in good agreement with the expected molar ratio. Both triads exhibit linear and nonlinear optical properties featuring an efficient energy transfer from the BODIPY donor to the porphyrin acceptor. The nonlinear upconverted emission properties of the triads were studied by two-photon excitation in the Near-infrared (NIR, 710-930 nm). The maximum two-photon absorption cross-section values for the triads (40-70 GM) are larger than those typically reported in this wavelength range for porphyrins and BODIPY. Both the green emission of BODIPY (approximate to 514 nm) and the red emission of porphyrins (650-750 nm) were observed under NIR excitation at 930 nm. The distinct features of triads, namely i) an extended absorption; ii) an efficient energy transfer and iii) the nonlinear upconverted emission featuring a large separation between the excitation and emission wavelengths could be beneficial for application in sensing and imaging procedures.
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