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Efficient Intersystem Crossing in the Tröger's Base Derived From 4-Amino-1,8-naphthalimide and Application as a Potent Photodynamic Therapy Reagent.
- Source :
-
Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2020 Mar 18; Vol. 26 (16), pp. 3591-3599. Date of Electronic Publication: 2020 Feb 27. - Publication Year :
- 2020
-
Abstract
- Intersystem crossing (ISC) was observed for naphthalimide (NI)-derived Tröger's base, and the ISC was confirmed to occur by a spin-orbital charge-transfer (SOCT) mechanism. Conventional electron donor/acceptor dyads showing SOCT-ISC have semirigid linkers. In contrast, the linker between the two chromophores in Tröger's base is rigid and torsion is completely inhibited, which is beneficial for efficient SOCT-ISC. Femtosecond transient absorption (TA) spectra demonstrated charge-separation and charge-recombination-induced ISC processes. Nanosecond TA spectroscopy confirmed the ISC, and the triplet state is long-lived (46 μs, room temperature). The ISC quantum yield is dependent on solvent polarity (8-41 %). The triplet state was studied by pulsed-laser-excited time-resolved EPR spectroscopy, and both the NI-localized triplet state and triplet charge-transfer state were observed, which is in good agreement with the spin-density analysis. The Tröger's base was confirmed to be a potent photodynamic therapy reagent with HeLa cells (EC <subscript>50</subscript> =5.0 nm).<br /> (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Details
- Language :
- English
- ISSN :
- 1521-3765
- Volume :
- 26
- Issue :
- 16
- Database :
- MEDLINE
- Journal :
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Publication Type :
- Academic Journal
- Accession number :
- 31916322
- Full Text :
- https://doi.org/10.1002/chem.201905248