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Paper | Regular issue | Vol 106, No. 6, 2023, pp.1003-1021
Published online, 17th May, 2023
DOI: 10.3987/COM-23-14856
Functionalization of Phenothiazine Derivatives by Ammonium Bridge

Hideki Hayashi,* Tadashi Ogawa, Hiroshi Seno, and Take-aki Koizumi

*Nagoya Municipal Industrial Research Institute, 3-4-41, Rokuban, Atsuta-ku, Nagoya 456-0058


Ammonium-bridged bis(promazine) type compounds (BA-PF6: [Y-N+Me2-CH2-R-CH2-N+Me2-Y]2+[PF6-]2, Y = 3-(phenothiazin-10-yl)propyl, 3-(5-oxophenothiazin-10-yl)propyl, 3-(2-chlorophenothiazin-10-yl)propyl, and 3-(5-oxo-2-chlorophenothiazin-10-yl)propyl; R = octane-1,8-diyl, 1,4-phenylene, biphenylene-4,4’-diyl, and 2,2'-bipyridine-4,4’-diyl) were prepared and the effects of the central R unit and side Y unit were investigated. The products’ optical and electrochemical properties showed the effect of the central and side unit, suggesting that the products had two independent functional groups in one molecule. X-Ray crystallographic analyses indicated that the spatial placement of the compounds was controlled by the central R unit, which behaves as a spacer without changing the properties of the molecules.