Symmetrical bis(fulvene) chromophores: model compounds for acceptor–donor–acceptor dye architectures

Abstract

A facile method for synthesizing conjugated bis(fulvenes) demonstrates tailorable optical band gaps and serves as a model dye system for new organic electronic applications.

Fulvenyl-Functionalized Polyisocyanides: Cross-Conjugated Electrochromic Polymers with Variable Optical and Electrochemical Properties

“…The chemistry of tria-, penta-, and heptafulvenes − and fulvalenes ,,− (Figure A), their synthetic preparation, and the study of their physical properties have been the subject of continuous interest throughout the past decades. These nonalternant hydrocarbons do not exhibit classic Hückel aromaticity but can form ionic species upon reduction (pentafulvenes) or oxidation (tria- and heptafulvenes) that experience substantial aromatic stabilization via cyclic delocalization.…”

Crystal structures of 6-cyclopropyl-1,3-diphenylfulvene and 6-(2,3-dimethoxynaphthyl)-1,3-diphenylfulvene

“…Pentafulvenes are a unique class of cross-conjugated organic molecules commonly synthesized using aldehyde and cyclopentadiene starting materials under a variety of conditions (Thiele, 1900;Stone & Little, 1984;Sieverding et al, 2019). Substituted and highly colored pentafulvenes are of particular interest because of their unique optical and thermal properties and for their potential use in electronic applications (Peloquin et al, 2012;Godman et al, 2016;Shurdha et al, 2014). In synthetic organometallic chemistry, the fulvene unit is known to coordinate to metals, forming organometallic complexes of varying hapticity (Peloquin et al, 2018;Ma et al, 2011Ma et al, , 2012Beckhaus, 2018).…”

Golden Age of Fluorenylidene Phosphaalkenes–Synthesis, Structures, and Optical Properties of Heteroaromatic Derivatives and Their Gold Complexes

“… 1 , 2 The combination of suitable donor and acceptor units often leads to interesting optical and electronic properties. 3 , 4 For example, 9,9-dialkylated fluorene derivatives ( Figure 1 , I ) have been used extensively as efficient π-spacers in the construction of photoluminescent materials, dyes for dye-sensitized solar cells, and other optoelectronic applications. 5 − 11 The dialkylation significantly enhances solubility and has an influence on molecular packing, e.g., π-stacking; however, it does not significantly alter the optical and electronic properties compared to the parent 2H-fluorene.…”