6533b7d3fe1ef96bd12613fe

RESEARCH PRODUCT

A Phenylene-Bridged Cyclohexa-meta-phenylene as Hexa-peri-hexabenzocoronene Precursor.

Bastian DumslaffDieter SchollmeyerAkimitsu NaritaManfred WagnerKlaus Müllen

subject

010405 organic chemistryOrganic ChemistryHexa-peri-hexabenzocoroneneGeneral Chemistry010402 general chemistry01 natural sciencesCatalysis0104 chemical scienceschemistry.chemical_compoundchemistryPhenyleneIntramolecular forcePolymer chemistrySpectroscopyDerivative (chemistry)

description

A phenylene-bridged cyclohexa-meta-phenylene was synthesized via intramolecular Yamamoto coupling of an appropriate p-quinquephenyl derivative carrying four m-chlorophenyl substituents. The structural proof could be obtained by single-crystal X-ray diffraction analysis, which also revealed a slightly strained structure with an internal phenylene bridge. Notably, this cyclo-meta-phenylene served as a novel precursor for hexa-peri-hexabenzocoronene (HBC). The cyclodehydrogenation proceeded smoothly, providing the corresponding HBC derivative as confirmed by MALDI-TOF-MS, and UV/Vis spectroscopy.

10.1002/chem.201801949https://pubmed.ncbi.nlm.nih.gov/29882611