Tetraphenylethene-Embedded Pillar[5]arene and [15]Paracyclophane: Distorted Cavities and Host-Guest Binding Properties

Yingtao Fan; Kaitai Hu; Junyi Nan; Yingzhong Shen

doi:10.3390/molecules26195915

Tetraphenylethene-Embedded Pillar[5]arene and [15]Paracyclophane: Distorted Cavities and Host-Guest Binding Properties

Molecules. 2021 Sep 29;26(19):5915. doi: 10.3390/molecules26195915.

Authors

Yingtao Fan¹, Kaitai Hu¹, Junyi Nan¹, Yingzhong Shen¹

Affiliation

¹ Applied Chemistry Department, College of Material Science & Engineering, Nanjing University of Aeronautics & Astronautics, Nanjing 210016, China.

Abstract

Two aggregation-induced emission (AIE) macrocycles (DMP[5]-TPE and PCP[5]-TPE) were prepared by embedding Tetraphenylethene (TPE) unit into the skeletons of Dimethoxypillar[5]arene (DMP[5]) and [15]Paracyclophane ([15]PCP) at meso position, respectively. In crystal, the PCP[5]-TPE showed a distorted cavity, and the incubation of hexane inside the DMP[5]-TPE cavity caused a distinct change in the molecular conformation compared to PCP[5]-TPE. There was no complexation between PCP[5]-TPE and 1,4-dicyanobutane (DCB). UV absorption experiments showed the distorted cavity of DMP[5]-TPE hindered association with DCB.

Keywords: [15]Paracyclophane; aggregation-induced emission; host–guest; meso functionalization; pillararene.

Grants and funding

1/CX/CSRD VA/United States