Synthesis, Structure, Spectroscopic, and Electrochemical Properties of Highly Fluorescent Phosphorus(V)–meso‐Triarylcorroles

Chemistry - A European Journal - Tập 18 Số 20 - Trang 6386-6396 - 2012
Avijit Ghosh1, Mangalampalli Ravikanth1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076, India

Tóm tắt

AbstractThe synthesis, spectroscopic, and electrochemical properties of seven new PV–meso‐triarylcorroles (1–7) are reported. Compounds 1–7 were prepared by heating the corresponding free‐base corroles with POCl3 at reflux in pyridine. Hexacoordinate PV complexes of meso‐triarylcorroles were isolated that contained two axial hydroxy groups, unlike the PV complex of 8,12‐diethyl‐2,3,7,13,17,18‐hexamethylcorrole, which was pentacoordinate, or the PV complex of meso‐tetraphenylporphyrin, which was hexacoordinate with two axial chloro groups. 1H and 31P NMR spectroscopy in CDCl3 indicated that the hexacoordinated PV–meso‐triarylcorroles were prone to axial‐ligand dissociation to form pentacoordinated PV–meso‐triarylcorroles. However, in the presence of strongly coordinating solvents, such as CH3OH, THF, and DMSO, the PV–meso‐triarylcorroles preferred to exist in a hexacoordinated geometry in which the corresponding solvent molecules acted as axial ligands. X‐ray diffraction of two complexes confirmed the hexacoordination environment for PV–meso‐triarylcorroles. Their absorption spectra in two coordinating solvents revealed that PV–meso‐triarylcorroles showed a strong band at about 600 nm together with other bands, in contrast to PV–porphyrins, which showed weak bands in the visible region. These compounds were easier to oxidize and more difficult to reduce compared to PV–porphyrins. These compounds were brightly fluorescent, unlike the weakly fluorescent PV–porphyrins, and the quantum yields for selected PV–corroles were as high as AlIII and GaIII corroles, which are the best known fluorescent compounds among oligopyrrolic macrocycles.

Từ khóa


Tài liệu tham khảo

 

10.1039/b618482k

10.1039/b805230c

10.1142/S1088424608000297

10.2174/157019305774322716

10.1055/s-2008-1078687

10.1002/1099-0690(200206)2002:11<1735::AID-EJOC1735>3.0.CO;2-K

10.1002/adsc.200303145

10.1142/S1088424609000668

10.1142/S1088424604000465

10.1021/ar700039y

10.1039/jr9650001620

10.1070/RC1980v049n11ABEH002527

10.1070/RC1983v052n07ABEH002871

Erben C., 2000, The Porphyrin Handbook Vol. 2, 233

Paolesse R., 2000, The Porphyrin Handbook Vol. 2, 201

10.1007/BFb0111331

 

10.1021/jp052047i

10.1039/b507979a

10.1021/ja101647t

10.1021/ja202692b

10.1021/ja801049t

10.1021/ic901164r

10.1562/2005-06-16-RA-577

 

10.1002/(SICI)1521-3757(19990517)111:10<1530::AID-ANGE1530>3.0.CO;2-D

10.1002/(SICI)1521-3773(19990517)38:10<1427::AID-ANIE1427>3.0.CO;2-1

10.1021/ol990739h

10.1039/a903247i

 

10.1007/s007750100273

10.1080/02603590600666256

10.1142/S1088424606000624

Aviezer D., 2000, Cancer Res., 60, 2973

10.1039/b916590h

10.1016/S0040-4039(03)01356-X

10.1007/s11095-005-9225-1

10.1021/ja045372c

10.1039/c0cc01989e

10.1002/ange.200601399

10.1002/anie.200601399

10.1039/b911278b

10.1021/cb900159n

J. Youn Hwang H. Agadjanian L. K. Medina‐Kauwe Z. Gross H. B. Gray K. Sorasaenee D. L. Farkas Prog. Biomed. Opt. Imaging2008 6859 68590G;

10.1073/pnas.0901531106

10.1002/chem.200900920

 

10.1021/ja9943243

10.1007/s007750100275

10.1002/1521-3757(20010601)113:11<2190::AID-ANGE2190>3.0.CO;2-H

10.1002/1521-3773(20010601)40:11<2132::AID-ANIE2132>3.0.CO;2-5

10.1021/ja0113697

10.1039/a900571d

10.1002/1521-3757(20001117)112:22<4211::AID-ANGE4211>3.0.CO;2-E

10.1002/1521-3773(20001117)39:22<4045::AID-ANIE4045>3.0.CO;2-P

10.1021/ic010723z

10.1016/S0040-4039(01)01717-8

10.1002/1521-3757(20001117)112:22<4214::AID-ANGE4214>3.0.CO;2-X

10.1002/1521-3773(20001117)39:22<4048::AID-ANIE4048>3.0.CO;2-7

 

10.1039/dt9810000855

10.1021/ic00038a005

10.1002/ange.19941060708

10.1002/anie.199407311

10.1021/ic960484t

10.1021/ic9509037

10.1021/ja00099a032

10.1002/ange.19971090410

10.1002/anie.199703571

10.1021/ja9814570

10.1039/b006299p

10.1021/ic990784l

10.1021/ic960334i

10.1021/ic801101k

10.1021/jp807734x

10.1021/ic1017032

 

10.1016/j.ccr.2010.09.013

10.1016/S0020-1693(00)88125-6

10.1016/0020-1650(74)80186-8

10.1021/ic00031a011

10.1021/ic200840m

10.1039/dt9950003617

10.1021/ja077785u

10.1021/ic900056n

10.1021/ic991361m

10.1021/ic980283k

 

10.1039/a801544i

10.1021/ic0010196

10.1002/1521-3765(20010302)7:5<1041::AID-CHEM1041>3.0.CO;2-8

 

10.1021/ic00145a008

10.1021/ic00155a007

10.1080/00958977708073043

10.1021/ic50215a021

10.1021/ja00446a018

10.1021/ic8010986

 

10.1021/ic00347a029

10.1021/ic00059a017

10.1021/ja904832j

10.1021/ja01044a018

10.1016/S0020-1693(00)90804-1

 

10.1021/ic991342c

10.1021/ic0504846

10.1007/BF03166220

10.1002/1521-3765(20020603)8:11<2595::AID-CHEM2595>3.0.CO;2-A

10.1002/ejic.200700184

10.1016/S0162-0134(00)00077-5

 

10.1002/ange.200502335

10.1002/anie.200502335

10.1002/ange.200601580

10.1002/anie.200601580

10.1142/S1088424603000057

10.1002/chem.200390136

Du R., 2009, Synlett, 2701

 

10.1021/ic1008736

10.1021/ic900744v

10.1021/ic0484506

 

10.1021/ic00192a024

10.1039/c39820001279

10.1021/ic801421a

 

10.1016/S0162-0134(01)00373-7

10.1016/j.cplett.2008.05.038

10.1039/b714894a

 

Turro N. J., 1978, Modern Molecular Photochemistry

J. B. Birks Photophysics of Aromatic Molecules Wiley Interscience New York 1970;

10.1007/978-1-4615-7658-7

10.1016/j.ica.2006.09.016

10.1107/S0108767307043930

10.1021/jo060007k

Thông tin
Thông tin xuất bản

Chemistry - A European Journal

Tập 18 Số 20

6386-6396

Thông tin tác giả