Efficient Intersystem Crossing in the Troger's Base Derived From 4-Amino-1,8-naphthalimide and Application as a Potent Photodynamic Therapy Reagent

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Zhao Y., Chen K., YILDIZ E., Li S., Hou Y., Zhang X., ...Daha Fazla

CHEMISTRY-A EUROPEAN JOURNAL, cilt.26, sa.16, ss.3591-3599, 2020 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 26 Sayı: 16
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1002/chem.201905248
  • Dergi Adı: CHEMISTRY-A EUROPEAN JOURNAL
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Agricultural & Environmental Science Database, Applied Science & Technology Source, Biotechnology Research Abstracts, Chimica, Compendex, EMBASE, MEDLINE
  • Sayfa Sayıları: ss.3591-3599
  • Anahtar Kelimeler: intersystem crossing, naphthalimides, photophysics, time-resolved spectroscopy, Troger's bases, TRIPLET-STATE FORMATION, PHOTOINDUCED ELECTRON-TRANSFER, BODIPY-ANTHRACENE DYADS, PHOTON UP-CONVERSION, TIME-RESOLVED EPR, EXCITED-STATE, SYMMETRY-BREAKING, SPIN POLARIZATION, CHARGE-TRANSFER, SINGLET OXYGEN
  • Ankara Üniversitesi Adresli: Evet

Özet

Intersystem crossing (ISC) was observed for naphthalimide (NI)-derived Troger'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 Troger'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 mu s, 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 Troger's base was confirmed to be a potent photodynamic therapy reagent with HeLa cells (EC50=5.0 nm).