A facile synthesis of elusive alkoxy-substituted hexa-peri-hexabenzocoronene.
Oxidative cyclodehydrogenation of hexakis(4-alkoxyphenyl)benzene produces a quantitative yield of an indenofluorene derivative rather than the expected alkoxy-substituted hexa-peri-hexabenzocoronene (HBC). The structure of the unexpected indenofluorene was established by X-ray crystallography. The mechanistic considerations for the formation of the indenofluorene derivative led us to devise an alternative synthesis of elusive alkoxy-substituted HBC-a potentially important, disk-shaped structure for the preparation of liquid crystalline materials for practical applications in the emerging areas of molecular electronics and nanotechnology.
Wadumethrige
Shriya H
SH
Department of Chemistry, Marquette University, Milwaukee, Wisconsin 53201, USA.
Rathore
Rajendra
R
D000438:Alcohols / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D005449:Fluorenes / Q000737:chemistry; D010084:Oxidation-Reduction; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D014867:Water / Q000737:chemistry
D000438:Alcohols; D005449:Fluorenes; D011083:Polycyclic Compounds; C059688:alkoxyl radical; C507240:hexa-peri-hexabenzocoronene; D014867:Water; C041509:fluorene