1281983-52-5Relevant academic research and scientific papers
Redox-switchable 20π-, 19π-, and 18π-electron 5,10,15,20-tetraaryl-5,15-diazaporphyrinoid nickel(II) complexes
Satoh, Takaharu,Minoura, Mao,Nakano, Haruyuki,Furukawa, Ko,Matano, Yoshihiro
, p. 2235 - 2238 (2016)
The first examples of air-stable 20π-electron 5,10,15,20-tetraaryl-5,15-diaza-5,15-dihydroporphyrins, their 18π-electron dications, and the 19π-electron radical cation were prepared through metal-templated annulation of nickel(II) bis(5-arylamino-3-chloro-8-mesityldipyrrin) complexes followed by oxidation. The neutral 20π-electron derivatives are antiaromatic and the cationic 18π-electron derivatives are aromatic in terms of the magnetic criterion of aromaticity. The meso N atoms in these diazaporphyrinoids give rise to characteristic redox and optical properties for the compounds that are not typical of isoelectronic 5,10,15,20-tetraarylporphyrins. N makes all the difference: Redox-switchable 20π-, 19π-, and 18π-electron 5,10,15,20-tetraaryl-5,15-diazaporphyrinoids are prepared through metal-templated annulation of NiII bis(dipyrrin) complexes followed by oxidation. The meso N atoms in these diazaporphyrinoids give rise to characteristic redox and optical properties for the compounds that are not typical of isoelectronic 5,10,15,20-tetraarylporphyrins.
Highly Regioselective α-Chlorination of the BODIPY Chromophore with Copper(II) Chloride
Zhou, Xin,Yu, Changjiang,Feng, Zeya,Yu, Yang,Wang, Jun,Hao, Erhong,Wei, Yun,Mu, Xiaolong,Jiao, Lijuan
supporting information, p. 4632 - 4635 (2015/09/28)
A general and efficient method for α-chlorination of 4,4′-difluoro-4-bora-3a,4a-diaza-s-indacenes (BODIPYs) has been developed using CuCl2 as chlorination reagent. The reaction is characterized by complete 3/5-positions of BODIPY regioselectivity. This unusual highly regioselective α-halogenation of BODIPY is in sharp contrast to previously reported halogenation methods which preferred to occur first at the 2,6-positions of BODIPY. This approach provides a straightforward, facile, and economical route to 3- and/or 5-chloroBODIPYs with various meso-groups (H, alkyl, and aryl) and their derivatives.
Metal-mediated synthesis of antiaromatic porphyrinoids from a BODIPY precursor
Sakida, Takafumi,Yamaguchi, Shigeru,Shinokubo, Hiroshi
, p. 2280 - 2283 (2011/04/21)
(Figure Presented) Metallic route to antiaromaticity: The synthesis of a butadiyne-bridged cyclic BODIPY dimer (see structure; C white, B orange, N blue, F green) and trimer was achieved through Pd-catalyzed Stille coupling and Cu-mediated Glaser-type coupling. These cyclic BODIPYs were found to be stable 24π- and 36π-antiaromatic porphyrinoids with planar conformations, and their structures, electronic states, and reactivity were explored.
