Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 40, Pages 22051-22056Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202109310
Keywords
chirality; helicenes; nanographenes; nonagonal carbocycle; polycyclic aromatic hydrocarbons
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Funding
- European Research Council (ERC) under the European Union [ERC-2015-STG-677023]
- Ministerio de Ciencia, Innovacion y Universidades (MICIU/FEDER/AEI, Spain) [PGC2018-101181-B-I00]
- Universidad de Granada (UGR) (Plan Propio - Intensificacion de la Investigacion) [PP2017-PRI.I-02]
- Swiss National Science Foundation [CRSK-2_190365]
- Universidad de Granada/CBUA
- Swiss National Science Foundation (SNF) [CRSK-2_190365] Funding Source: Swiss National Science Foundation (SNF)
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A new family of chiral saddle-helix hybrid nanographenes was reported, including the synthesis of hexa-peri-hexabenzocoronene analogues with a nine-membered carbocycle and pi-extended carbo[n]helicenes containing a nine-membered ring. These compounds exhibit a significant distortion from planarity and improved photophysical properties compared to other saddle-helix hybrids, making them the most twisted helicenes reported to date.
A new family of chiral saddle-helix hybrid nanographenes is reported. The first hexa-peri-hexabenzocoronene (HBC) analogues bearing a nine-membered carbocycle are presented. Furthermore, for the first time, pi-extended carbo[n]helicenes containing a nine-membered ring as part of the helical moiety have been synthesized. The combination of a [5]helicene moiety and a nonagon ring in a single chiral motif induces a tremendous distortion from planarity into the nanographenic structures compared to other saddle-helix hybrids such as heptagon- and octagon-containing pi-extended carbo[5]helicenes. In fact, the interplanar angle of the two terminal rings reaches the largest angle (134.8 degrees) of a carbohelicene reported to date, thus being by far the most twisted helicene yet prepared. Photophysical properties evaluation showed improved absorption dissymmetry factors (|g(abs)|=4.2x10(-3)) in the new family of nonagon-containing pi-extended carbo[5]helicenes.
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