Tris(2-hydroxyphenyl)triazasumanene ((A)-(+)-1), a bowl-shaped molecule, which possesses 2-(2′-hydroxyphenyl)pyridine moieties, was successfully synthesised. (A)-(+)-1 showed a single peak emission in CH₂Cl₂, which overlapped with the emission of the triazasumanene skeleton and diminished at a high concentration, corresponding to the formation of the excited enol form. In contrast, single crystals of (A)-(+)-1 exhibited a dual emission with a large Stokes shift, indicating the presence of the excited keto form by the excited state intramolecular proton transfer (ESIPT) process. In the solution of (A)-(+)-1 containing a mixture of a large amount of a poor solvent (hexane or MeOH) and a small amount of CH₂Cl₂, colloidal aggregates emerged with the continuous increment of emission intensity by further addition of the poor solvent, demonstrating aggregation-induced enhanced emission (AIEE). The analysis of the morphology and the structure of the aggregates using a scanning electron microscope (SEM) and powder X-ray diffraction (PXRD) revealed the well-ordered structure of the aggregates, which possessed a molecular packing pattern similar to that of an (A)-(+)-1 single crystal.

中文翻译：

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Tris（2-hydroxyphenyl）triazasumanene：碗形激发态分子内质子转移（ESIPT）荧光团与聚集诱导的增强发射（AIEE）†

成功地合成了具有2-（2'-羟基苯基）吡啶部分的碗状分子三（2-羟基苯基）三氮杂苏曼烯（（A）-（+）- 1）。（A）-（+）- 1在CH ₂ Cl _2中显示出一个单峰发射，该峰与三氮杂苏曼烯骨架的发射重叠，并且在高浓度下减小，这对应于激发的烯醇形式的形成。相反，（A）-（+）- 1的单晶表现出具有大的斯托克斯位移的双重发射，表明通过激发态分子内质子转移（ESIPT）过程存在激发的酮形式。在（A）-（+）-在含有大量不良溶剂（己烷或MeOH）和少量CH ₂ Cl ₂的混合物的图1中，通过进一步添加不良溶剂，胶体聚集体随着发射强度的连续增加而出现，证明了聚集诱导的增强作用。排放量（AIEE）。使用扫描电子显微镜（SEM）和粉末X射线衍射（PXRD）分析聚集体的形态和结构，发现聚集体的结构井然有序，其分子堆积模式类似于（A）-（+）- 1单晶。