Baumgärtner Kevin, Kirschbaum Tobias, Krutzek Fabian, Dreuw Andreas, Rominger Frank, Mastalerz Michael
Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
Interdisziplinäres Zentrum für Wissenschaftliches Rechnen, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 205, 69120, Heidelberg, Germany.
Chemistry. 2017 Dec 14;23(70):17817-17822. doi: 10.1002/chem.201703988. Epub 2017 Nov 16.
Extended fused aromatic compounds are promising materials for organic electronics. Among them, structures with five-membered annulated rings differ from those consisting only of six-membered carbocyclic rings. To date, fusion of five-membered rings has been realized mainly via the [b]-edge, and systems fused via the [c]-edge are of low stability. Whereas linearly double [b]-fused systems are stable, analogous [c]-fused systems have not been described to date. Comparable to the stabilization of longer acenes by peri-fusion, herein the synthesis of doubly [c]-annulated systems stabilized by double peri-fusion is described. The compounds were analyzed by X-ray crystallography, photophysical methods, and DFT calculations to gain deeper insight into the nature of conjugation in these new systems.
扩展稠合芳香化合物是有机电子学中有前景的材料。其中，含有五元稠环的结构不同于仅由六元碳环组成的结构。迄今为止，五元环的稠合主要通过[b]边实现，而通过[c]边稠合的体系稳定性较低。虽然线性双[b]稠合体系是稳定的，但类似的[c]稠合体系迄今为止尚未见报道。与通过周边稠合使较长的并苯稳定化类似，本文描述了通过双周边稠合稳定的双[c]稠合体系的合成。通过X射线晶体学、光物理方法和密度泛函理论计算对这些化合物进行了分析，以更深入地了解这些新体系中共轭的本质。
