Abstract
We developed a new benzodifuran derivative as the condensation product between 2,6-diamino-4-(4-nitrophenyl)benzo[1,2-b:4,5-b’]difuran-3,7-dicarboxylate and 3-hydroxy-2-naphthaldehyde. The intramolecular hydrogen-bond interactions in the terminal half-salen moieties produce a sterically encumbered highly conjugated main plane and a D-A-D (donor-acceptor-donor) T-shaped structure. The novel AIEgen (aggregation-induced enhanced emission generator) fulfils the requirement of RIR (restriction of intramolecular rotation) molecules. DR/NIR (deep red/near infrared) emission was recorded in solution and in the solid state, with a noteworthy photoluminescence quantum yield recorded on the neat crystals which undergo some mechanochromism. The crystal structure study of the probe from data collected at a synchrotron X-ray source shows a main aromatic plane π-stacked in a columnar arrangement.
Highlights
In recent years, the design and synthesis of organic fluorescent dyes highly performant in the solid state have received researcher’s widespread attention [1,2,3,4]
We investigated its photophysical properties and correlated the data to its single crystal structure resolved from data collected at synchrotron source
Different reaction conditions were experimented by varying BDF/3-hydroxy-2-naphthaldehyde ratio, the solvent and the operating temperature
Summary
The design and synthesis of organic fluorescent dyes highly performant in the solid state have received researcher’s widespread attention [1,2,3,4]. Of particular interest are AIE fluorophores with intense emission at DR/NIR region owing to their deep tissue penetration, photo-stability and minimum interference in living systems [25,29,30] Their applications are closely related to cell imaging and DNA and protein sensing [31,32,33]. Benzodifuran derivatives have drawn attention for a wide range of biological and pharmacological applications, including antimicrobial, antiviral, analgesic and antitumor [37,38,39,40] activity This class of heterocyclic compounds are employed in dyes industry as pigments and in different fields of optoelectronics and photonics. 3-hydroxy-2-naphthaldehyde moieties, i.e., the fragment depicted in red
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