PIFA-promoted intramolecular oxidative cyclization of pyrrolo- and indolo[1,2- a ]quinoxalino-appended porphyrins: an efficient synthesis of meso ,β-pyrrolo- and indolo[1,2- a ]quinoxalino-fused porphyrins.

Autor: Kumar B; Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India. dalipk@pilani.bits-pilani.ac.in., Khandagale SB; Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India. dalipk@pilani.bits-pilani.ac.in., Verma N; Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India. dalipk@pilani.bits-pilani.ac.in., Pandurang TP; Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India. dalipk@pilani.bits-pilani.ac.in., Iype E; College of Engineering and Technology, American University of the Middle East, Kuwait., Kumar D; Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India. dalipk@pilani.bits-pilani.ac.in.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2022 Sep 14; Vol. 20 (35), pp. 7040-7046. Date of Electronic Publication: 2022 Sep 14.
DOI: 10.1039/d2ob01272c
Abstrakt: We have developed an efficient protocol for the synthesis of meso ,β-pyrrolo- and indolo[1,2- a ]quinoxalino-fused porphyrin systems 7-9 by PIFA-promoted intramolecular oxidative cyclization of easily accessible meso -pyrrolo- and indolo[1,2- a ]quinoxalino-appended porphyrins 6a-j. The absorption spectra of meso ,β-pyrrolo- and indolo[1,2- a ]quinoxalino-fused porphyrins 7-9 displayed bathochromic shifted (100-150 nm) and broadened Soret bands and Q bands in addition to intense band near IR region. The indolo[1,2- a ]quinoxalino-fused porphyrin 9bZn with lower fluorescence quantum yield (0.003) and reduced energy gap (∼1.3 eV) was found to sensitize singlet oxygen effectively.
Databáze: MEDLINE