Müller J, Müller J, Buck J, Hirsch A (2023)
Publication Type: Journal article
Publication year: 2023
Book Volume: 26
Article Number: e202201310
Within the scope of this paper, nine π-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.
APA:
Müller, J., Müller, J., Buck, J., & Hirsch, A. (2023). Carpet Beater Molecules: Synthesis and Characterization of Functional Hexa-peri-benzocoronene–Alkyne Coupling Products. European Journal of Organic Chemistry, 26. https://dx.doi.org/10.1002/ejoc.202201310
MLA:
Müller, Johannes, et al. "Carpet Beater Molecules: Synthesis and Characterization of Functional Hexa-peri-benzocoronene–Alkyne Coupling Products." European Journal of Organic Chemistry 26 (2023).
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