Regioselective Synthesis of Methylene-Bridged Naphthalene Oligomers and Their Host–Guest Chemistry

In
this research, we report the regioselective synthesis of methylene-bridged
naphthalene oligomers from 2,6-dialkoxyl naphthanene and paraformaldehyde
by using p-TsOH as the catalyst and CH2Cl2 as the solvent. The structures were characterized
by NMR spectroscopy and X-ray crystallography. Their host–guest
chemistry with organic cations was studied, and optimal naphthalene
numbers in the oligomers were revealed for different guests. In addition,
the reason for the unsuccessful synthesis of methylene-bridged naphthalene
macrocycles was discussed.

本研究报道了以2,6-二烷氧基萘与多聚甲醛为原料，对甲苯磺酸(p-TsOH)为催化剂、二氯甲烷(CH2Cl2)为溶剂，通过区域选择性反应合成亚甲基桥联萘低聚物的方法。通过核磁共振(NMR)光谱与X射线晶体学对产物结构进行了表征；研究了该类低聚物与有机阳离子的主客体化学行为，并明确了针对不同客体时低聚物的最优萘环数目。此外，本文还探讨了亚甲基桥联萘大环合成失败的原因。