Synthesis, properties and singlet oxygen generation of thiazolidinone double bond linked porphyrin at meso and β-position
Synthesis, properties and singlet oxygen generation of thiazolidinone double bond linked porphyrin at meso and β-position
复制标题
DOI：
10.1039/c6ra03489f
复制
发表时间：
2016-01-01
期刊：
影响因子：
3.9
通讯作者：
Chauhan, S. M. S.
中科院分区：
文献类型：
--
作者：
Ahmad, Sohail;Yadav, Kumar Karitkey;Chauhan, S. M. S.
以取代胺、二硫化碳、氯乙酸乙酯和卟啉醛为原料，采用一锅四组分Knoevenagel缩合法合成了中位和β -取代游离碱和锌金属化噻唑烷酮-卟啉偶联物。通过IR、H-1 NMR、C-13 NMR、UV-Vis、荧光光谱和HRMS光谱对这些新合成的共轭物进行了表征。研究了这些卟啉偶联物的单线态产氧行为，发现这些卟啉偶联物属于II型单线态氧。荧光和单线态氧量子产率之间的中取代（单，二，四）和取代-偶联物进行了检查。进一步分析了这些新型有机光催化剂对萘酚和呋喃的光催化氧化反应，发现中四取代（Zn3a）和β取代（Zn6a）卟啉在单线态氧的生成和光催化氧化反应中效率较高。
Meso and beta-substituted free base and zinc metallated thiazolidinone-porphyrin conjugates were synthesized by one pot four component Knoevenagel condensation by utilizing substituted amines, carbon disulfide, ethyl chloroacetate and porphyrin aldehydes. These newly synthesized conjugates were characterized by IR, H-1 NMR, C-13 NMR, UV-Vis, fluorescence and HRMS spectroscopy. The singlet oxygen generation behaviors of these porphyrin conjugates were studied and it was observed that these porphyrin conjugates followed type II singlet oxygen. Fluorescence and singlet oxygen quantum yields among meso-substituted (mono-, di, tetra) and beta-substituted conjugates were examined. The photocatalytic photooxidation of naphthols and furan by using these new organic photocatalysts were further analysed and it was observed that meso-tetra substituted (Zn3a) and beta-substituted (Zn6a) porphyrins are much efficient for generation of singlet oxygen and for photocatalytic photooxidation.