The Synthesis and Mesophases Studies of a Novel Discotic Compound Containing Two Triphenylene Cores Linked by Crown Ether

Abstract

In this study, a novel discotic compound based on triphenylene core were synthesized. 6,7,10,11-tetrapentyloxy-2-hydroxy-3-methoxy triphenylene was synthesized via the common synthisis route including the Williamson Etherification of catechol, the iodination of 1,2-dipentyloxybenzene, the Ullman Coupling and the coupling of 3,3′-4,4′-tetrapentyloxy diphenyl and methoxy-phenol;Bis-(8-bromooctanoyl)-dibenzo-18-crown-6 was obtained from 8-bromooctanoic acid and dibenzo-18-crown-6 in polyphosphoric acid and then reacted in Et₃SiH with trifluoroacetic acid as catalyst to obtain bis-(8-bromooctyl)-dibenzo-18-crown-6. Bis-(8-bromooctyl)-dibenzo-18-crown-6 reacted with 6,7,10,11-tetrapentyloxy-2-hydroxy-3-methoxy triphenylene via Williamson reaction to produce the goal product. The chemical structures of the compounds were identified by using fourier transform infrared spectroscopy, nuclear magnetic resonance and the thermal properties were characterized by optical polarizing microscope and differential scanning calorimeter.

Keywords:

• DSC calorimetry
• mesophases
• POM picture
• triphenylene

Acknowledgment

This work was supported by Beijing Municipal Education Commission Project under Grant (No. KM201110015003), the Key (Key grant) Project of Chinese Ministry of Education (No 211004), Beijing Municipal party committee Organization department project under Grant (No. 2010D005004000006) and PHR (HLB) (Project No.: PHR20090515).