Synthesis of phosphorescent asymmetrically π-extended porphyrins for two-photon applications.
Synthesis of phosphorescent asymmetrically π-extended porphyrins for two-photon applications.
复制标题
DOI：
10.1021/jo501521x
复制
发表时间：
2014-09-19
期刊：
影响因子：
--
通讯作者：
Vinogradov SA
中科院分区：
文献类型：
--
作者：
Esipova TV;Vinogradov SA
Significant effort has been directed in recent years toward porphyrins with enhanced two-photon absorption (2PA). However, the properties of their triplet states, which are central to many applications, have rarely been examined in parallel. Here we report the synthesis of asymmetrically π-extended platinum(II) and palladium(II) porphyrins, whose 2PA into single-photon-absorbing states is enhanced as a result of the broken center-of-inversion symmetry and whose triplet states can be monitored by room-temperature phosphorescence. 5,15-Diaryl-syn-dibenzoporphyrins (DBPs) and syn-dinaphthoporphyrins (DNPs) were synthesized by [2 + 2] condensation of the corresponding dipyrromethanes and subsequent oxidative aromatization. Butoxycarbonyl groups on the meso-aryl rings render these porphyrins well-soluble in a range of organic solvents, while 5,15-meso-aryl substitution causes minimal nonplanar distortion of the macrocycle, ensuring high triplet emissivity. A syn-DBP bearing four alkoxycarbonyl groups in the benzo rings and possessing a large static dipole moment was also synthesized. Photophysical properties (2PA brightness and phosphorescence quantum yields and lifetimes) of the new porphyrins were measured, and their ground-state structures were determined by DFT calculations and/or X-ray analysis. The developed synthetic methods should facilitate the construction of π-extended porphyrins for applications requiring high two-photon triplet action cross sections.
登录
查看更多内容
影响因子：
19
作者：
Borisov, Sergey M.;Larndorfer, Christoph;Klimant, Ingo
通讯作者：
Klimant, Ingo
影响因子：
15
作者：
Filatov, Mikhail A.;Lebedev, Artem Y.;Mukhin, Sergei N.;Vinogradov, Sergei A.;Cheprakov, Andrei V.
通讯作者：
Cheprakov, Andrei V.
影响因子：
1.4
作者：
CALLIS, JB;GOUTERMAN, M;HENDERSON, BH
通讯作者：
HENDERSON, BH
影响因子：
4
作者：
Baluschev, S.;Yakutkin, V.;Cheprakov, A.
通讯作者：
Cheprakov, A.
影响因子：
35
作者：
Collins, Hazel A.;Khurana, Mamta;Anderson, Harry L.
通讯作者：
Anderson, Harry L.