Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, 1060, Vienna, Austria.
X-Ray Center, TU Wien, Getreidemarkt 9, 1060, Vienna, Austria.
Chemistry. 2019 Mar 21;25(17):4412-4425. doi: 10.1002/chem.201805578. Epub 2019 Feb 27.
The preparation and characterization of 12 azaindolo[3,2,1-jk]carbazoles is presented. Ring-closing C-H activation allowed for the convenient preparation of six singly and six doubly nitrogen-substituted indolo[3,2,1-jk]carbazole derivatives in which ten of the materials have not been described in the literature before. The detailed photophysical and electrochemical characterization of the developed materials revealed a significant impact of the incorporation of pyridine-like nitrogen into the fully planar indolo[3,2,1-jk]carbazole backbone. Furthermore, the nitrogen position decisively impacted intermolecular hydrogen bonding and thus the solid-state alignment. Ultimately, the versatility of the azaindolo[3,2,1-jk]carbazoles scaffold makes this class of materials an attractive new building block for the design of functional organic materials.
本文介绍了 12 种氮杂吲哚并[3,2,1-jk]咔唑的制备和表征。通过闭环 C-H 活化，方便地制备了 6 种单取代和 6 种双取代的氮杂吲哚并[3,2,1-jk]咔唑衍生物，其中有 10 种材料以前在文献中没有描述过。对所开发材料的详细光物理和电化学特性进行了表征，结果表明将吡啶型氮原子引入完全平面的吲哚并[3,2,1-jk]咔唑骨架中会产生显著影响。此外，氮原子的位置还会决定性地影响分子间氢键，从而影响固态排列。最终，氮杂吲哚并[3,2,1-jk]咔唑骨架的多功能性使得这类材料成为设计功能有机材料的一个有吸引力的新结构单元。
