吡咯并[1,2-a]喹喔啉和吲哚并[1,2-a]喹喔啉稠合卟啉的 PIFA 促进的分子内氧化环化：β-吡咯并[1,2-a]喹喔啉和吲哚并[1,2-a]喹喔啉稠合卟啉的有效合成。
PIFA-promoted intramolecular oxidative cyclization of pyrrolo- and indolo[1,2-]quinoxalino-appended porphyrins: an efficient synthesis of ,β-pyrrolo- and indolo[1,2-]quinoxalino-fused porphyrins.
机构信息
Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India.
College of Engineering and Technology, American University of the Middle East, Kuwait.
出版信息
Org Biomol Chem. 2022 Sep 14;20(35):7040-7046. doi: 10.1039/d2ob01272c.
We have developed an efficient protocol for the synthesis of ,β-pyrrolo- and indolo[1,2-]quinoxalino-fused porphyrin systems 7-9 by PIFA-promoted intramolecular oxidative cyclization of easily accessible -pyrrolo- and indolo[1,2-]quinoxalino-appended porphyrins 6a-j. The absorption spectra of ,β-pyrrolo- and indolo[1,2-]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-]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.
我们开发了一种高效的合成方法，通过 PIFA 促进的易于获得的 -吡咯并[1,2-]喹喔啉基和吲哚并[1,2-]喹喔啉基稠合卟啉 6a-j 的分子内氧化环化反应，合成了,β-吡咯并[1,2-]喹喔啉和吲哚并[1,2-]喹喔啉稠合卟啉系统 7-9。,β-吡咯并[1,2-]喹喔啉和吲哚并[1,2-]喹喔啉稠合卟啉 7-9 的吸收光谱显示出红移（100-150nm）和拓宽的 Soret 带和 Q 带，以及近红外区域的强带。吲哚并[1,2-]喹喔啉稠合卟啉 9bZn 的荧光量子产率（0.003）较低，能隙（约 1.3eV）降低，被发现能有效地敏化单线态氧。
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