10.1021/acs.inorgchem.6b01371.s003
Yuxiang Chen
Yuxiang
Chen
Wenjuan Fang
Wenjuan
Fang
Kang Wang
Kang
Wang
Wei Liu
Wei
Liu
Jianzhuang Jiang
Jianzhuang
Jiang
Nonperipheral Tetrakis(dibutylamino)phthalocyanines.
New Types of 1,8,15,22-Tetrakis(substituted)phthalocyanine Isomers
American Chemical Society
2016
THF
refluxing n
single-crystal X-ray diffraction analyses
isolation
C 4
tetraki
2016-08-31 11:50:37
Dataset
https://acs.figshare.com/articles/dataset/Nonperipheral_Tetrakis_dibutylamino_phthalocyanines_New_Types_of_1_8_15_22-Tetrakis_substituted_phthalocyanine_Isomers/3795915
Cyclic
tetramerization of 3-(dibutylamino)phthalonitrile in refluxing <i>n</i>-pentanol in the presence of magnesium pentanoate afforded
the four regioisomer-containing nonperipheral 1,8-/11,15-/18,22-/25-tetrakis(dibutylamino)phthalocyaninato
magnesium complexes with the 1,8,15,22-tetrakis(dibutylamino)phthalocyanine
isomer Mg{Pc[α-N(C<sub>4</sub>H<sub>9</sub>)<sub>2</sub>]<sub>4</sub>-<i>C</i><sub>4</sub>} (<b>2</b>). This, in
combination with its much superior crystallinity over the remaining
three isomers, renders the easy isolation of <b>2</b> only through
two simple recrystallizations from THF and methanol. Treatment of <b>2</b> with trifluoroacetic acid induced the isolation of metal-free
1,8,15,22-tetrakis(dibutylamino)phthalocyanine, H<sub>2</sub>{Pc[α-N(C<sub>4</sub>H<sub>9</sub>)<sub>2</sub>]<sub>4</sub>-<i>C</i><sub>4</sub>} (<b>1</b>), which further reacted with M(OAc)<sub>2</sub>·<i>n</i>H<sub>2</sub>O (M = Ni, Zn) in refluxing <i>n</i>-pentanol, giving the 1,8,15,22-tetrakis(dibutylamino)phthalocyaninato
metal complexes M{Pc[α-N(C<sub>4</sub>H<sub>9</sub>)<sub>2</sub>]<sub>4</sub>-<i>C</i><sub>4</sub>} (M = Ni (<b>3</b>), Zn (<b>4</b>)). The full series of four 1,8,15,22-tetrakis(dibutylamino)phthalocyanine
isomeric compounds have been characterized by a series of spectroscopic
methods and single-crystal X-ray diffraction analyses. Obviously,
the present result provides a simple and effective pathway for the
synthesis and isolation of novel 1,8,15,22-tetrakis(dibutylamino)phthalocyanine
isomeric derivatives, providing one step forward toward completing
bis(alkyl)amino-incorporated phthalocyanine species.