Stimuli-responsive luminescent materials have attracted considerable attention in recent years because of their potential application in various fields. In this work, dimethylamine substituted bisbenzocoumarin (DB-Cn) derivatives are synthesized and their optical properties are investigated. These molecules show solvatochromic and mechanochromic properties. Powder wide-angle X-ray diffraction and differential scanning calorimetry curves reveal that the initial crystalline states are transformed to amorphous states under various external stimuli. Single crystal X-ray analysis of DB-C2 reveals that the destruction of the crystal conformation and the changes of intermolecular π–π stacking interactions could be responsible for the red-shifted emission. Further investigation revealed that DB-C2 showed acidochromic properties and could be utilized as a security ink. The control 1H NMR experiment reveals that the protonation of the aromatic amines is essential for the acidochromic properties. This work provides information on the mechanism study of stimuli-responsive luminescence properties of binaphthalene-type luminescent materials and expands the potential application of these materials.

Dimethylamine substituted bisbenzocoumarins: solvatochromic, mechanochromic and acidochromic properties

Considering highly valuable biological and pharmaceutical properties of coumarins, the synthesis of these heterocycles has been considered for many organic and pharmaceutical chemists This review includes the recent research in synthesis methods of coumarin systems, investigating their biological properties and describing the literature reports for the period of 2016 to the middle of 2020 In this review, we have classified the contents based on co-groups of coumarin ring These reported methods are carried out in the classical and non-classical conditions particularly under green condition such as using green solvent, catalyst and other procedures

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Overview on developed synthesis procedures of coumarin heterocycles

Dimethylamino naphthalene-based cyanostyrene derivatives with stimuli responsive luminescent properties

A coumarin-based portable fluorescent probe for rapid turn-on detection of amine vapors

Luminescent organic materials with tunable emission color have attracted much attention for their potential application in multiple fields. Herein, we designed and synthesized a series of dimethylamine substituted binaphthanol based organic fluorophores. Decorating with substituents at the alkene moiety on the binaphthanol core backbone led to organic solid emitters with color tunability from the blue to red regions. These fluorophores exhibited solvatochromic properties and two compounds (DB-4 and DB-5) showed aggregation-induced emission properties. The binaphthanol core structure induced a twisted molecular conformation and special intermolecular packing mode in a single crystal structure, which was beneficial for the inhibition of the strong intermolecular π–π stacking interaction and induced the AIE feature as well as the fluorescence emission in the solid state. The absorption and emission changes of these molecules under acidic and basic conditions revealed that they had acidochromic properties and could be used as security ink. This work provided a new strategy for the synthesis of organic solid emitters with tunable emissions based on the simple binaphthanol core backbone.

Binaphthanol-based organic fluorophores with color tunability and their optical properties

Synthesis and studies of axial chiral bisbenzocoumarins: Aggregation-induced emission enhancement properties and aggregation-annihilation circular dichroism effects.

Wei Liu

Papers

Synthesis and studies of axial chiral bisbenzocoumarins: Aggregation-induced emission enhancement properties and aggregation-annihilation circular dichroism effects.