Modular Design Of Fluorescent Dibenzo- And Naphtho-Fluoranthenes: Structural Rearrangements And Electronic Properties

Abstract

A library of 12 dibenzo- and naphtho-fluoranthene polycyclic aromatic hydrocarbons (PAHs) with MW = 302 (C24H14) was synthesized via a Pd-catalyzed fluoranthene ring-closing reaction. By understanding the various modes by which the palladium migrates during the transformation, structural rearrangements were bypassed, obtaining pure PAHs in high yields. Spectroscopic and electrochemical characterization demonstrated the profound diversity in the electronic structures between isomers. Highlighting the significant differences in emission of visible light, this library of PAHs will enable their standardization for toxicological assessment and potential use as optoelectronic materials.

Publication Date

8-3-2018

Publication Title

Journal of Organic Chemistry

Volume

83

Issue

15

Number of Pages

8036-8053

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1021/acs.joc.8b00891

Socpus ID

85047551579 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/85047551579

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