Synthesis and characterization of poly[2,3,9,10,16,17,23,24‐octakis(dodecyloxycarbonyl)phthalocyaninatogermoxane]

Abstract

In this article we describe the preparation of poIy[2,3,9,10,16,17,23,24-octakis(dodecyloxycarbonyl)phthalocyaninatogermoxane] by thermal polycondensation of 2,3,9,10,16,17,23,24-octakis(dodecyloxycarbony1)phthalocyaninatogermanium dihydroxide, and its characterization. The average molar mass of the resulting polymer was determined. High molar masses are assessible, e. g., aw = 360000 g/mol, a, = 140000 g/mol, at moderate temperature for the polycondensation (200°C). The polymer shows a liquid-crystalline phase in an extremely large temperature range. Furthermore, Langmuir-Blodgett films (LB films) of the polymer and of the monomer were prepared and characterized. In LB films the phthalocyanine rings are preferentially oriented normal to the dipping direction. 0 1993, Huthig & Wepf Verlag, Basel CCC 0025-1 16)</93/$05.00

Soluble and Liquid‐Crystalline Ovalenes

“…However, this method is less efficient with longer, less‐polar alcohols and bromoalkanes such as 2‐ethylhexanol and 1‐bromo‐2‐ethylhexane and gave only low yields after exceedingly long reaction times (on the order of a week). By modifying a procedure reported for the esterification of phthalocyanine‐2,3,6,7,10,11,14,15‐octacarboxylic acid16 we succeeded in obtaining high yields of the 2‐ethylhexyl esters 10 b and 8 b (Scheme , R=2‐ethylhexyl) overnight by esterification with 2‐ethylhexanol and 1‐bromo‐2‐ethylhexane in acetonitrile in the presence of the strong soluble base 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU).…”

Synthesis and Structural Features

“…A series of liquid crystalline esters of 2,3,9,10,16,17,23,24-phthalocyanine octacarboxylic acid have been synthesized by Dulog and Gittinger [205]. The octacarboxylic acid is prepared [206] from benzenetetracarbonitrile (tetracyanobenzene) 12051 in two steps: cyclization under standard conditions, and hydrolysis of phthalocyanineoctacarbonitrile with potassium hydroxide in triethylene glycol.…”

“…Synthesis of peripherally substituted octa(alkoxycarbony1)phthalocyanines [205]. Reagents: lumnar mesophase (Dho) from below room temperature to above 300 "C.…”

Mesogenic Behaviour of 2,3,9,10,16,17,23,24-Octadodecyloxycarbonyl- phthalocyaninatogermanium-dihydroxide

“…Another endothermic peak at 170.9"C was caused by the polycondensation of the investigated compound to the corresponding poly(germoxane) . 4 Because of that polycondensation in the mesophase no clearing point could be observed up to this temperature. As in the case of the metal-free 2,3,9,10,16,17,23 ,24-octaalkoxycarbonylphthalocyaninesl the range of existence of the mesophase of the discotic liquid crystal presented in this study compared to other liquid crystalline phthalocyanine~~-~~ is extraordinarily large.…”