螺旋烯
化学
天青
构象异构
溶剂变色
Knoevenagel冷凝
对映体
二聚体
吲哚嗪
区域选择性
级联反应
氢键
结晶学
四聚体
光化学
立体化学
分子
有机化学
酶
催化作用
作者
Yimin Liang,Shangshang Wang,Min Tang,Lin Wu,Liping Bian,Liang Jiang,Zheng‐Bin Tang,Jiali Liu,Aocong Guan,Zhichang Liu
标识
DOI:10.1002/anie.202218839
摘要
Abstract We report here the one‐pot synthesis of benzo[1,2‐ a : 3,4‐ a ′ : 5,6‐ a ′′]triazulene ( BTA ), wherein three azulene units are embedded through a tandem reaction comprising two steps, Suzuki coupling and Knoevenagel condensation, between a readily available triborylated truxene precursor and 8‐bromo‐1‐naphthaldehyde. Its nitration leads to a regioselective trinitrated product, namely, BTA ‐ NO 2 . Single‐crystal X‐ray crystallography revealed that the superstructure of BTA consists of a dimer stacked by two enantiomeric helicene conformers, while that of BTA ‐ NO 2 consists of an unprecedented π‐tetramer stacked from two enantiomeric dimers, that is, four distinct helicene conformers. Both compounds show excellent stability and fluorescence with large Stokes shifts of up to 5100 cm −1 . In addition, BTA ‐ NO 2 exhibits a unique solvatochromic effect in different solvents and hydrogen‐bonding‐induced emission transfer in different ratios of THF/H 2 O solutions.
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