%0 Journal Article %1 Schnitzlein_2021 %A Schnitzlein, Matthias %A Mützel, Carina %A Shoyama, Kazutaka %A Farrell, Jeffrey M. %A Würthner, Frank %D 2021 %I Wiley %J Eur. J. Org. Chem. %K myown %N 5 %R 10.1002/ejoc.202101273 %T PAHs Containing both Heptagon and Pentagon: Corannulene Extension by 5+2 Annulation %U https://doi.org/10.1002%2Fejoc.202101273 %V 2022 %X Utilizing Pd-catalyzed 5+2 annulation a series of heptagon-extended corannulenes could be synthesized from a borinic acid precursor furnished by C−H borylation strategy. Single-crystal X-ray analysis revealed the presence of two conformational enantiomers crystallizing in a racemic mixture. Through their embedded five- and seven-membered rings these polycyclic aromatic hydrocarbons (PAHs) exhibit both negative and positive curvature and UV/Vis/NIR absorption spectroscopy as well as cyclic voltammetry experiments provided insights into the influence of larger flanking aromatic systems and electron-donating substituents encompassing the heptagonal ring. Through 5+2 annulation of acenaphthylene an azulene-containing PAH with intriguing optoelectronical properties including a very small bandgap and absorption over the whole visible spectrum could be obtained. Theoretical calculations were employed to elucidate the long-wavelength absorption and aromaticity.

@article{Schnitzlein_2021, abstract = {Utilizing Pd-catalyzed [5+2] annulation a series of heptagon-extended corannulenes could be synthesized from a borinic acid precursor furnished by C−H borylation strategy. Single-crystal X-ray analysis revealed the presence of two conformational enantiomers crystallizing in a racemic mixture. Through their embedded five- and seven-membered rings these polycyclic aromatic hydrocarbons (PAHs) exhibit both negative and positive curvature and UV/Vis/NIR absorption spectroscopy as well as cyclic voltammetry experiments provided insights into the influence of larger flanking aromatic systems and electron-donating substituents encompassing the heptagonal ring. Through [5+2] annulation of acenaphthylene an azulene-containing PAH with intriguing optoelectronical properties including a very small bandgap and absorption over the whole visible spectrum could be obtained. Theoretical calculations were employed to elucidate the long-wavelength absorption and aromaticity.}, added-at = {2022-04-08T09:50:52.000+0200}, author = {Schnitzlein, Matthias and Mützel, Carina and Shoyama, Kazutaka and Farrell, Jeffrey M. and Würthner, Frank}, biburl = {https://www.bibsonomy.org/bibtex/246857088cf9b67d6c993efd8e65cd9c3/wuerthner_group}, doi = {10.1002/ejoc.202101273}, interhash = {7fbef37d10fc8d3d42483e4511990a9b}, intrahash = {46857088cf9b67d6c993efd8e65cd9c3}, journal = {Eur. J. Org. Chem.}, keywords = {myown}, month = dec, number = 5, publisher = {Wiley}, timestamp = {2023-05-23T13:08:43.000+0200}, title = {PAHs Containing both Heptagon and Pentagon: Corannulene Extension by [5+2] Annulation}, url = {https://doi.org/10.1002%2Fejoc.202101273}, volume = 2022, year = 2021 }