Cao Haishi, Chang Virginia, Hernandez Randy, Heagy Michael D
Department of Chemistry, New Mexico Institute of Mining & Technology, Socorro, NM 87801, USA.
J Org Chem. 2005 Jun 24;70(13):4929-34. doi: 10.1021/jo050157f.
A 3 x 14 matrix of substituted N-aryl-1,8-naphthalimides was synthesized for the evaluation and discovery of dual fluorescence. Because of their unique photophysical properties, these dual fluorescent systems represent an exception to the widely studied TICT (Twisted Internal Charge Transfer) fluorescent dyes or tautomeric benzofluorescein class of two-color dyes. The matrix library was designed to investigate the effects of heterocycles, particularly pi-excessive and pi-deficient systems. Of the 42 compounds surveyed, five displayed well-resolved two-color emission in solvents as nonpolar as hexane. Based on the observed trends in fluorescence lambda(max) and quantum yield, a new model is proposed that predicts LW and SW emission for these systems. In addition, this model provides potential design features for the synthesis of new dual fluorescent species.
合成了一个由取代的N-芳基-1,8-萘二甲酰亚胺组成的3×14矩阵，用于评估和发现双重荧光。由于其独特的光物理性质，这些双荧光体系是广泛研究的TICT（扭曲内电荷转移）荧光染料或互变异构苯并荧光素类双色染料的一个例外。该矩阵库旨在研究杂环的影响，特别是富π和缺π体系的影响。在所研究的42种化合物中，有5种在与己烷一样非极性的溶剂中表现出分辨率良好的双色发射。基于观察到的荧光λ(max)和量子产率趋势，提出了一个新模型，该模型预测这些体系的长波和短波发射。此外，该模型为新型双荧光物种的合成提供了潜在的设计特征。
