Monophosphaporphyrins:: Oxidative π-extension at the peripherally fused carbocycle of the phosphaporphyrin ring

被引:41
作者
Matano, Yoshihiro [1 ]
Nakashima, Makoto [1 ]
Nakabuchi, Takashi [1 ]
Imahori, Hiroshi [1 ,2 ]
Fujishige, Shinya [3 ]
Nakano, Haruyuki [3 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Mol Engn, Nishikyo Ku, Kyoto 6158510, Japan
[2] Kyoto Univ, Inst Integrated Cell Mat Sci, Kyoto 6158510, Japan
[3] Kyushu Univ, Grad Sch Sci, Dept Chem, Fukuoka 8128581, Japan
关键词
D O I
10.1021/ol7029118
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 18 pi-sigma(3)- and 22 pi-sigma(4)-phosphaporphyrins were successfully prepared by an acid-promoted condensation between a phosphatripyrrane and a 2,5-bis[hydroxy(phenyl)methyl]pyrrole, and their structures, aromaticity, and optical and electrochemical properties were disclosed. Notably, a sigma(4)-phosphaporphyrinogen and the 18 pi-sigma(3)-phosphaporphyrin undergo oxidative pi-extension at the peripherally fused carbocycle to afford the 22 pi-sigma(4)-phosphaporphyrin.
引用
收藏
页码:553 / 556
页数:4
相关论文
共 48 条
[11]  
2-H
[12]   A density functional study of the ground state electronic structure of phosphorus-porphyrins [J].
Delaere, D ;
Nguyen, MT .
CHEMICAL PHYSICS LETTERS, 2003, 376 (3-4) :329-337
[13]   Structure-property relationships in phosphole-containing π-conjugated systems:: A quantum chemical study [J].
Delaere, D ;
Nguyen, MT ;
Vanquickenborne, LG .
JOURNAL OF PHYSICAL CHEMISTRY A, 2003, 107 (06) :838-846
[14]   Synthesis and X-ray crystal structure of a p-confused carbaporphyrinoid [J].
Duan, Zheng ;
Clochard, Magali ;
Donnadieu, Bruno ;
Mathey, Francois ;
Tham, Fook S. .
ORGANOMETALLICS, 2007, 26 (15) :3617-3620
[15]   Synthesis and luminescence of soluble meso-unsubstituted tetrabenzo- and tetranaphtho[2,3]porphyrins [J].
Finikova, OS ;
Cheprakov, AV ;
Vinogradov, SA .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9562-9572
[16]   Confusion, inversion, and creation - a new spring from porphyrin chemistry [J].
Furuta, H ;
Maeda, H ;
Osuka, A .
CHEMICAL COMMUNICATIONS, 2002, (17) :1795-1804
[17]   N-CONFUSED PORPHYRIN - A NEW ISOMER OF TETRAPHENYLPORPHYRIN [J].
FURUTA, H ;
ASANO, T ;
OGAWA, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (02) :767-768
[18]   Doubly N-confused porphyrin: A new complexing agent capable of stabilizing higher oxidation states [J].
Furuta, H ;
Maeda, H ;
Osuka, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (05) :803-807
[19]   Theoretical study of stability, structures, and aromaticity of multiply N-confused porphyrins [J].
Furuta, H ;
Maeda, H ;
Osuka, A .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25) :8563-8572
[20]   Facile oxidative rearrangement of dispiro-porphodimethenes to nonplanar and sheetlike porphyrins with intense absorptions in the near-IR region [J].
Gill, HS ;
Harmjanz, M ;
Santamaría, J ;
Finger, I ;
Scott, MJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (04) :485-490