Gupta Ravindra Kumar, Achalkumar Ammathnadu S
Department of Chemistry , Indian Institute of Technology Guwahati , Guwahati , Assam 781039 , India.
J Org Chem. 2018 Jun 15;83(12):6290-6300. doi: 10.1021/acs.joc.8b00161. Epub 2018 May 24.
A high yielding microwave-assisted synthetic method to obtain unsymmetrical perylene diester monoimide (PEI) by treating the perylene tetrester (PTE) with a requisite amine is reported. Perylene-based molecules are widely used in the construction of self-assembled supramolecular structures because of their propensity to aggregate under various conditions. In comparison to perylene bisimides (PBIs), PEIs are less studied in organic electronics/self-assembly due to the synthetic difficulty and low yields in their preparation. PEIs are less electron deficient and have an unsymmetric structure in comparison to PBIs. Further, the PEIs have a higher solubility than PBIs. The present method is applicable with a wide range of substrates like aliphatic, aromatic, benzyl amines, PTEs, and bay-annulated PTEs. This method provides a tuning handle for the optical/electronic properties of perylene derivatives and also provides an easy access to unsymmetrical PBIs from the PEIs.
报道了一种高产率的微波辅助合成方法，通过用所需的胺处理苝四酯（PTE）来获得不对称苝二酯单酰亚胺（PEI）。基于苝的分子由于其在各种条件下易于聚集，被广泛用于构建自组装超分子结构。与苝双酰亚胺（PBI）相比，由于PEI合成困难且产率低，在有机电子学/自组装方面的研究较少。与PBI相比，PEI的缺电子性较低且结构不对称。此外，PEI的溶解度高于PBI。本方法适用于多种底物，如脂肪族、芳香族、苄胺、PTE和湾区稠合PTE。该方法为苝衍生物的光学/电子性质提供了一种调节手段，也为从PEI轻松获得不对称PBI提供了途径。
