Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 26, Issue 9, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202201310
Keywords
acetylene bridge; interaction; mono-substituted hexa-peri-benzocoronene; pi- substituent effects; Sonogashira coupling
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This paper presents nine pi-expanded mono-substituted 5,8,11,14,17-pentakis-(tert-butyl)-hexa-peri-hexabenzocoronenes (HBC) and explores their synthesis method and the influence of substitution groups on their optoelectronic properties.
Within the scope of this paper, nine pi-expanded mono-substituted 5,8,11,14,17-pentakis-(tert-butyl)-hexa-peri-hexabenzocoronenes (HBC) are introduced. 2-Iodo-5,8,11,14,17-pentakis-(tert-butyl)-hexa-peri-hexabenzocoronene served as precursor and was reacted with ethynyltrimethylsilane in a Sonogashira coupling reaction. The acetylene unit is used as a linker and can undergo another Sonogashira coupling reaction combining different phenyl coupling partners with the HBC core. The electron-withdrawing groups such as nitrile, pyridine and carbonyl species (aldehyde, methylester, carboxylic acid) as well as the three quinoxaline based species (diphenylquinoxaline, dibenzo[a,c]phenazine, phenanthro[4',5'-a,b,c]phenazine) serve as substitution moieties. Their influence on the optoelectronic properties were investigated by UV/Vis absorption spectroscopy demonstrating a maximum redshift of 7 nm compared to starting compound 2-Iodo-5,8,11,14,17-pentakis-(tert-butyl) HBC. As for the phenanthro[4',5'-a,b,c]phenazine substituted HBC a dramatic decrease in the intensity of the absorption of the UV/Vis spectrum was observed. The fluorescence spectroscopy pointed out that the dibenzo[a,c]phenazine and phenanthro[4',5'-a,b,c]phenazine substitution changed the spectra to one broad peak departing from the characteristic HBC-like emission pattern.
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