Pyrene Appended Free-base, Phosphorus(V) and Gallium(III) Corroles and Their β,β′-Linked Corrole Dimers: Synthesis, Photophysical and Electrochemical Properties

被引:16
作者
Sujesh, S. [1 ]
Basumatary, Biju [1 ]
Kumar, Amit [1 ]
Sankar, Jeyaraman [1 ]
机构
[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal Bypass Rd, Bhopal 462066, MP, India
关键词
Corrole; Pyrene; Dimer; Gallium; Phosphorous;
D O I
10.1002/ejic.202000807
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Pyrene appended free-base, phosphorus(V) and gallium (III) corrole conjugates were synthesized and characterized. Efficient beta-beta ' dimerization of corroles was achieved by oxidation with p-chloranil in moderate yield from their respective metallated corroles. The weak ground state electronic coupling between pyrene and corrole units was established by photophysical and electrochemical investigations. The fluorescence spectral studies showed a red shifted emission maximum for dimer with respect to their monomeric counterpart due to possible pi-conjugation and supported by the density functional theory (DFT). The electrochemical investigation revealed multiple oxidation associated with the corrole and pyrene centers.
引用
收藏
页码:540 / 547
页数:8
相关论文
共 78 条
[11]   DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].
BECKE, AD .
JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652
[12]  
Bendix J, 2000, ANGEW CHEM INT EDIT, V39, P4048, DOI 10.1002/1521-3773(20001117)39:22<4048::AID-ANIE4048>3.0.CO
[13]  
2-7
[14]   Electrochemical Study of Pyrene on Glassy Carbon Electrode Modified with Metal-Oxide Nanoparticles and Graphene Oxide/Multi-Walled Carbon Nanotubes Nanoplatform [J].
Boikanyo, Diseko ;
Adekunle, Abolanle S. ;
Ebenso, Eno E. .
JOURNAL OF NANO RESEARCH, 2016, 44 :158-195
[15]   Osmium-nitrido corroles as NIR indicators for oxygen sensors and triplet sensitizers for organic upconversion and singlet oxygen generation [J].
Borisov, Sergey M. ;
Alemayehu, Abraham ;
Ghosh, Abhik .
JOURNAL OF MATERIALS CHEMISTRY C, 2016, 4 (24) :5822-5828
[16]  
Br?ckner, 2001, SYNLETT, P442
[17]   Syntheses, Crystal Structure, and Spectroscopic Properties of Meso-Meso-Linked Porphyrin-Corrole Hybrids [J].
Chen, Chen ;
Zhu, Yi-Zhou ;
Fan, Qiao-Jun ;
Song, Hai-Bin ;
Zheng, Jian-Yu .
CHEMISTRY LETTERS, 2013, 42 (08) :936-938
[18]   Corrole-BODIPY conjugates: enhancing the fluorescence and phosphorescence of the corrole complex via efficient through bond energy transfer [J].
Chen, Wei ;
Zhang, Jianfeng ;
Mack, John ;
Kubheka, Gugu ;
Nyokong, Tebello ;
Shen, Zhen .
RSC ADVANCES, 2015, 5 (63) :50962-50967
[19]   Unusual Interchromophoric Interactions in β,β′ Directly and Doubly Linked Corrole Dimers: Prohibited Electronic Communication and Abnormal Singlet Ground States [J].
Cho, Sung ;
Lim, Jong Min ;
Hiroto, Satoru ;
Kim, Pyosang ;
Shinokubo, Hiroshi ;
Osuka, Atsuhiro ;
Kim, Dongho .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (18) :6412-6420
[20]   Microwave-assisted synthesis of corroles [J].
Collman, JP ;
Decréau, RA .
TETRAHEDRON LETTERS, 2003, 44 (06) :1207-1210