Würthner Frank, Ahmed Shahadat, Thalacker Christoph, Debaerdemaeker Tony
Abteilung Organische Chemie II Universität Ulm Albert-Einstein-Allee 11, 89081 Ulm, Germany.
Chemistry. 2002 Oct 18;8(20):4742-50. doi: 10.1002/1521-3765(20021018)8:20<4742::AID-CHEM4742>3.0.CO;2-L.
Highly colored and photoluminescent naphthalene bisimide dyes have been synthesized from 2,6-dichloronaphthalene bisanhydride 1 by means of a stepwise nucleophilic displacement of the two chlorine atoms by alkoxides and/or alkyl amines. The alkoxy-substituted derivatives are yellow dyes with green emission and low photoluminescence quantum yields, whereas the amine-substituted derivatives exhibit a color range from red to blue with strong photoluminescence up to 76%. Structure-property relationships for this class of two-dimensional chromophores were evaluated based on a single-crystal X-ray analysis for dye 5a, the observed solvatochromism, and quantum-chemical calculations. Owing to the simple tuning of the absorption properties over the whole visible range by the respective substituents, the pronounced brilliancy, and the intense photoluminescence, this class of dyes is considered to be highly suited for numerous applications such as fluorescent labeling of biomacromolecules and light-harvesting in supramolecular assemblies. As an important step towards such applications efficient FRET (fluorescence resonance energy transfer) has been demonstrated for a covalently tethered bichromophoric compound that contains a red and a blue naphthalene bisimide dye.
通过用醇盐和/或烷基胺逐步亲核取代2,6 - 二氯萘二酐1中的两个氯原子，合成了颜色鲜艳且具有光致发光性能的萘二酰亚胺染料。烷氧基取代的衍生物是具有绿色发射和低光致发光量子产率的黄色染料，而胺基取代的衍生物呈现从红色到蓝色的颜色范围，强光致发光高达76%。基于染料5a的单晶X射线分析、观察到的溶剂化显色现象和量子化学计算，评估了这类二维发色团的结构-性质关系。由于通过各自的取代基可以在整个可见范围内简单地调节吸收特性、具有显著的亮度和强烈的光致发光，这类染料被认为非常适合多种应用，如生物大分子的荧光标记和超分子组装体中的光捕获。作为迈向此类应用的重要一步，已证明一种含有红色和蓝色萘二酰亚胺染料的共价连接双发色团化合物具有高效的荧光共振能量转移（FRET）。
