Self‐Catalyzed Hydroxyl‐Yne Click Reaction: A Powerful Tool toward Red‐Emitting Nontraditional Small Organic Luminogens

Abstract

Nontraditional small organic luminogens (NTSOLs) without classic conjugated chromophores have attracted significant attention. However, the design and synthesis of NTSOLs with fluorescence in the red region remain significantly challenging. In this study, we established a self‐catalyzed hydroxyl‐yne click reaction for preparing long‐wavelength and red‐emitting NTSOLs. Owing to their perfect reaction selectivity, high efficiency, and excellent universality, a series of compounds with well‐defined structures were obtained in high yields. Moreover, the obtained compounds showed concentration‐enhanced and excitation‐dependent emission characteristics. The compounds also exhibited dramatical chemical structure‐dependent and aggregation‐induced red‐shifted fluorescence properties, based on which we successfully obtained red‐emitting NTSOLs by simply adjusting chemical structure and concentration. Also, the compounds show good cell staining ability, which can be used in cell imaging.

Designing Nonconventional Luminescent Materials with Efficient Emission in Dilute Solutions via Modulation of Dynamic Hydrogen Bonds

“…NLMs without aromatic groups which exhibit CTE properties are often used for cell imaging due to their low toxicity [ 46 , 47 , 48 , 49 ]. To validate the potential of P1 for cell imaging and labelling applications, we used standard methylthiazolyl diphenyltetrazolium bromide (MTT) assays to evaluate the cytotoxicity of P1 at different concentrations on HeLa cells.…”

X‐yne click polymerization

“…For example, very recently, Jiang and coworkers found that self-catalyzed hydroxyl-yne click polymerization could be realized in the presence of tertiary amine-containing alcohols, which could serve as both monomers and internal bases during the polymerization process. [123,124] The introduction of nitrogen atoms into alcohol monomers allows this polymerization to occur without an external base catalyst. Furthermore, activated alkynes mentioned above generally result in the partially conjugated polymers by X-yne click polymerizations.…”

In Situ Growth of Columnar PEG on PEDOT and Its Antifouling Properties

“…This allows for the rapid and controlled formation of complex molecular structures with high precision. Moreover, these reactions can be carried out under mild conditions, which minimizes undesirable side reactions and limits the amount of unwanted byproducts. − …”