Department of Chemistry, SRM Institute of Science and Technology, Kattankulathur, Chennai 603203, India.
Institute of Chemistry, The Hebrew University of Jerusalem, Edmond J. Safra Campus, Jerusalem 91904, Israel.
Molecules. 2023 Jun 28;28(13):5074. doi: 10.3390/molecules28135074.
The synthesis of multiply substituted acenes is still a relevant research problem, considering their applications and future potential. Here we present an elegant synthetic protocol to afford tetra-peri-substituted naphthalene and tetracene from their tetrahalo derivatives by a Pd(0)-catalyzed C-C cross-coupling method in a single step. The newly synthesized tetracenes were characterized by NMR, HRMS, UV-vis spectrophotometry, and single-crystal X-ray diffraction (SCXRD). In addition, the first systematic computational study of the effect of chalcogenophenyl substitutions on the chiroptical properties of twistacenes was reported here. The gas phase computational studies using density functional theory (DFT) on a series of chalcogenophene-substituted tetracenes revealed that their chiroptical activity could be systematically increased via the atomistic tuning of peripheral substituents.
多取代并苯的合成仍然是一个相关的研究问题，考虑到它们的应用和未来的潜力。在这里，我们提出了一个优雅的合成方案，通过 Pd(0)催化的 C-C 交叉偶联反应，从它们的四卤代衍生物一步合成四取代萘和四并苯。新合成的四并苯通过 NMR、HRMS、UV-vis 分光光度法和单晶 X 射线衍射（SCXRD）进行了表征。此外，这里还首次系统地报道了杂芳基取代对扭曲并苯手性光学性质影响的计算研究。使用密度泛函理论（DFT）在一系列杂芳基取代的四并苯上的气相计算研究表明，通过外围取代基的原子调整，可以系统地增加它们的手性活性。
