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Pagoda[5]arene with Large and Rigid Cavity for the Formation of 1∶2 Host-Guest Complexes and Acid/Base-Responsive Crystalline Vapochromic Properties

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CCS Chemistry 2022年第1期4卷 318-330页

作者： Xiao-Ni Han Qian-Shou Zong Ying Han Chuan-Feng Chen Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of Molecular Recognition and FunctionInstitute of ChemistryChinese Academy of SciencesBeijing 100190 University of the Chinese Academy of Sciences Beijing 100049 College of Biological Chemical Sciences and EngineeringJiaxing UniversityJiaxing 314001

Pagoda[5]arene(P5),which is composed of five 2,6-dimethoxylanthracene(2,6-DMA)subunits bridged by methylene groups at 1,5 positions,was conveniently synthesized in 43%by trifluoroacetic acid(TFA)-catalyzed one-pot condensation of commercially available 2,6-DMA and paraformaldehyde in 1,2-dichlorobenzene(o-DCB)at room temperature.P5 showed a highly symmetrical pentagonal structure with a large and deep electron-rich cavity,which made it form stable 1∶2 host–guest complexes with various aryl-pyridinium,bipyridinium,and stilbazolium salts in solution.Interestingly,P5 could complex two or even three guests with its intrinsic cavity and the pseudocavity formed by the adjacent macrocycles in solid states.Moreover,the strong intermolecular charge-transfer(ICT)interactions between P5 and the guests were observed.Especially,the complexes formed by P5 and the protonated pyridinium or bipyridinium salts showed acid/base-responsive color changes in solution and remarkable crystalline vapochromic properties by two kinds of processes:from ICT to no ICT and from ICT to enhanced ICT interaction or vice versa.We believe that the easily available P5 with the specific structure and intriguing 1∶2 host–guest complexation can find wide application in supramolecular assemblies and functional materials.

关键词： supramolecular chemistry macrocyclic arene pagodaarene host-guest complexation ICT interaction vapochromic property

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