Synthesis of Benzo[k]fluoranthene Derivatives through Diels–Alder Reaction of 1,3‐Diarylbenzo[c]furans

Abstract

Diels–Alder reaction of symmetrical/unsymmetrical benzo[c]furans with acenaphthylene in xylenes at reflux temperatures followed by p‐toluenesulfonic acid‐mediated epoxide cleavage and dehydration furnished diaryl/heteroaryl‐substituted benzo[k]fluoranthenes. This strategy could be successfully applied to the synthesis of dimeric and trimeric benzo[k]fluoranthenes. Functionalization of representative benzo[k]fluoranthene derivatives was also performed. UV/Visible, emission and electrochemical properties of representative fluoranthene derivatives are also reported.

Substitution Pattern-Controlled Fluorescence Lifetimes of Fluoranthene Dyes

“…In principle, sets of lifetime labels with lifetimes spanning about 1–50 ns are optimum. Most organic dyes, however, have lifetimes <10 ns or even <5 ns, and most short-lived QDs contain cadmium. , This encouraged us to assess the potential of fluoranthene dyes as lifetime labels, as these compounds are known to have high Φ fl , , a low sensitivity to microenvironment polarity, , and fluorescence lifetimes in the range of 5–44 ns, , depending on substitution pattern. Fluoranthene with the molecular formula C 16 H 10 consists of a naphthalene and a benzene moiety, linked by a 5-membered ring.…”

Diels–Alder Reaction of Isobenzofurans/Cyclopentadienones with Tetrathiafulvalene: Preparation of Naphthalene, Fluoranthene, and Fluorenone Derivatives

“…However, it should be noted that the half-TTF, 1,3-dithiol-2-thione, as well as TTF are not well-known for their dienophilic character. Our recent report on inverse-electron-demand Diels–Alder reaction of benzo­[ c ]­furans with acenaphthylene prompted us to explore the reaction of the same with an electron-rich dienophile, TTF. As expected, the reaction of 1,3-diphenylbenzo­[ c ]­furan 1a with TTF 2 in dry xylenes at reflux for 6 h furnished Diels–Alder adduct 3a as a brown solid in an excellent yield (Scheme ).…”