2,5‐Dimethoxybenzene‐1,4‐dicarboxaldehyde: An Emissive Organic Crystal and Highly Efficient Fluorescent Waveguide

Abstract

To identify the simplest organic structure for an emitter, we focused on 2,5‐dimethoxybenzene‐1,4‐dicarboaldehyde. This symmetric molecule has a very low molecular weight (MW=194), a single benzene unit, and consists of only three elements (H, C and O). It forms highly efficient and pure emitting crystals (λem=499 nm, ΦF=0.42, FWHM=42 nm) due to the rigid structure based on the single benzene framework and four intramolecular hydrogen bonds between electron‐donating methoxy and electron‐accepting aldehyde groups. This crystal acts as a good optical waveguide with pure green emission (FWHM=34 nm) and very low loss coefficient (0.00120 dB/μm).

Following the light: 3D-printed COF@poly(2-hydroxyethyl methacrylate) dual emissive composite with response to polarity and acidity

“…DMTA is an efficient fluorophore in organic solvents and solid state and its fluorescence is attributed to the formation of hydrogen bonds that rigidify the structure. 55 Thus, exfoliation of the material is able to restore this emission, mainly in acidic medium, which seems to be related with the protonation of the nitrogen atoms in the imine groups ( vide infra ). It was observed that the intensity and position of both emission bands depend on the THF/water ratio.…”

Facile investigation of reversible nanostructure changes in flexible crystals

“…1a) was obtained from 4-bromobenzyl cyanide and 2,5-dimethoxybenzene-1,4-dicarboxaldehyde. 25 Reddish orange-colored needle-like crystals were grown from 1,2-dichloroethane (Fig. 1b).…”

Achieving two things at one stroke: crystal engineering simultaneously optimizes the emission and mechanical compliance of organic crystals

“…19 Single benzene emitters have been widely investigated and they can readily form high-quality crystals. [48][49][50][51][52] By employing a single benzene emitter 1, here we report two organic polymorphs that display quite different emission and mechanical properties. Two crystals 1B and 1G were obtained by screening various crystallization conditions.…”