1338801-07-2Relevant academic research and scientific papers
Preparation and optical and electrochemical properties of octaethylphthalocyanines fused with several tetrathiafulvalene units
Kimura, Takeshi,Watanabe, Dai,Namauo, Toshiharu
experimental part, p. 605 - 611 (2011/12/15)
3,6-Diethylphthalonitrile (3) with a tetrathiafulvalene (TTF) unit at 4,5-positions was prepared from 4,5-xylylenedithio-3,6-diethylphthalonitrile (1a) via elimination of the xylylene group, connection of a carbonyl group to benzenedithiolate generated, and condensation of 4,5-bis(methylthio)-1,3- dithiole-2-thione with benzo-1,3-dithiole-2-one (2-O) produced. A 1:1 mixture of phthalonitrile (3) and 4,5-bis(benzylthio)-3,6-diethylphthalonitrile (1b) was treated with lithium in n-hexanol at 120°C to produce hexakis (benzylthio)mono(tetrathiafulvaleno)phthalocyanine (5), tetrakis(benzylthio) bis(tetrathiafulvaleno)phthalocyanine (6), and bis(benzylthio) tris(tetrathiafulvaleno)phthalocyanine (7). The structures of 5, 6, and 7 were determined by 1H NMR, FAB MS, MALDI-TOF MS (matrix assisted laser desorption ionization time-of-flight mass spectrometry), and UV - vis spectroscopy. Compound 6 is a mixture of trans and cis isomers (6-trans and 6-cis). The UV - vis spectrum of 5 measured in chloroform changed by addition of trifluoroacetic acid (TFA). The Q band absorption at λmax = 755 nm (chloroform) decreased in intensity and resulted in a new absorption at λmax = 740 nm (chloroform/TFA). The electrochemical properties of 5, 6, and 7 were determined by cyclic voltammetry using Ag/AgNO3 as a reference electrode. Copyright
