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O-annulation to polycyclic aromatic hydrocarbons: a tale of optoelectronic properties from five- to seven-membered rings

Ðorđević, Luka, Milano, Domenico, Demitri, Nicola and Bonifazi, Davide 2020. O-annulation to polycyclic aromatic hydrocarbons: a tale of optoelectronic properties from five- to seven-membered rings. Organic Letters 22 (11) , pp. 4283-4288. 10.1021/acs.orglett.0c01331
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Abstract

We take advantage of the Pummerer oxidative annulation reaction to extend PAHs through the formation of an intramolecular C–O bond with a suitable phenol substituent. Depending on the peripheral topology of the PAH precursor (e.g., pyrene, boron–dipyrromethene, or perylene diimide) five-, six-, and seven-membered O-containing rings could be obtained. The effect of the O-annulations on the optoelectronic properties were studied by various methods with the pyrano-annulated pyrene and BODIPY derivatives depicting quantitative emission quantum yields.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: American Chemical Society
ISSN: 1523-7060
Date of First Compliant Deposit: 27 May 2020
Date of Acceptance: 13 May 2020
Last Modified: 02 Jul 2020 10:32
URI: http://orca-mwe.cf.ac.uk/id/eprint/131943

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