Aggregation‐Induced Emission of Multiphenyl‐Substituted 1,3‐Butadiene Derivatives: Synthesis, Properties and Application

Abstract

Organic functional materials, including conjugated molecules and fluorescent dyes, have been intensely developed in recent years because they can be applied in many fields, such as solar cells, biosensing and bioimaging, and medical adjuvant therapy. Organic functional materials with aggregation-induced emission or aggregation-enhanced emission (AIE/AEE) characteristics have increasingly attracted attention due to their high quantum efficiency in the aggregated or solid state. A large variety of AIE/AEE materials have been designed and applied during the exponential growth of research interest in the abovementioned fields. Multiphenyl-substituted 1,3-butadiene (MPB), as a core structure that includes tetraphenyl-1,3-butadiene, hexaphenyl-1,3-butadiene and their derivatives, show a typical AIE/AEE feature and can be potentially used in all the above-mentioned fields. This review summarizes the design principles, the corresponding syntheses, and the structure-property relationships of MPBs, as well as their excellent innovative functionalities and applications. This review will be useful for scientists conducting chemistry, materials, and biomedical research in AIE/AEE-related fields.

Aggregation‐Induced Emission Properties of Copper Iodide Clusters

“…The mechanism at the origin of the AIE properties displayed by the two copper iodide clusters can be attributed to suppression of nonradiative decay in the aggregate states, as generally stated for organic molecules and metal‐based complexes . This agrees with DFT calculations performed for these clusters.…”

“…Indeed, these compounds generally possess twisted conformations and the restriction of intramolecular motions in the solid state, which block nonradiative decay channels, intensifies their emission. In recent years, the great development of AIE compounds is related to multiple potential applications, including luminescent probes for biomedical imaging and sensing applications, which are under intensive development …”

“…In recenty ears, the great development of AIE compounds is relatedtomultiple potential applications, including luminescent probes for biomedical imaging and sensing applications, which are under intensive development. [9][10][11][12][13][14][15][16][17][18] Because of their twisted conformations, AIE-active organic molecules usually aggregate into al oosely( defective) packed solid state that facilitates their transformation between differ-ent molecular arrangements. This characteristicc onfers an enhanced sensitivity to externals timuli and, in particular, to mechanical forces onto thesec ompounds.…”

Synthesis, photophysical and electropolymerization properties of thiophene-substituted 2,3-diphenylbuta-1,3-dienes

“…Buta-1,3-diene unit, which is prevalent in many biologically active natural compounds and pharmarceuticals, [39][40][41][42][43][44][45] has recently emerged as an interesting conjugated building block for the design of AIE or aggregation-enhanced emission (AEE) luminophores, allowing to extend π-conjugation of TPE 46 . In this respect, multiphenyl-substituted 1,3-butadienes (MPBs) have recently received increasing attention 47,48 . Noteworthy examples of this class of AIE (AEE) luminophores are 1,1,4,4-tetraphenylbuta-1,3-diene (TPB), a well-known highly efficient blue-emitting material [49][50][51][52][53] and 1,1,2,3,4,4-hexaphenylbuta-1,3-diene (HPB), which possess a helical structure like polyacetylene.…”

Stereospecific Synthesis of Multi-Aryl Substituted Olefins and 1,3-Dienes via 1,4-Palladium Migration/Suzuki Coupling Sequence

“…Despite the advancements in stereoselective synthesis of multi-substituted olefins 10,11 and 1,3-dienes, 12,13 effective synthetic approaches toward multi-aryl-substituted ones remain to be limited, in which the application of symmetric starting material or a homo-coupling reaction is necessary to overcome the geometric problem. 14,15 Therefore, a more agile synthetic strategy to greatly expand the toolbox for advanced material discovery is highly desirable.…”