Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic Applications

Abstract A dimeric fluorescent macrocycle m‐TPE Di‐EtP5 (meso‐tetraphenylethylene dimeric ethoxypillar[5]arene) is synthesized based on the meso‐functionalized ethoxy pillar[5]arene. Through the connectivity of two pillar[5]arenes by CC double bond, the central tetraphenylethylene (TPE) moiety is s...

Full description

Bibliographic Details
Main Authors: Kaiya Wang, Rongbo Zhang, Zejing Song, Kaituo Zhang, Xueqi Tian, Srikala Pangannaya, Minzan Zuo, Xiao‐Yu Hu
Format: Article
Language:English
Published: Wiley 2023-03-01
Series:Advanced Science
Subjects:
Online Access:https://doi.org/10.1002/advs.202206897
_version_ 1797860830803394560
author Kaiya Wang
Rongbo Zhang
Zejing Song
Kaituo Zhang
Xueqi Tian
Srikala Pangannaya
Minzan Zuo
Xiao‐Yu Hu
author_facet Kaiya Wang
Rongbo Zhang
Zejing Song
Kaituo Zhang
Xueqi Tian
Srikala Pangannaya
Minzan Zuo
Xiao‐Yu Hu
author_sort Kaiya Wang
collection DOAJ
description Abstract A dimeric fluorescent macrocycle m‐TPE Di‐EtP5 (meso‐tetraphenylethylene dimeric ethoxypillar[5]arene) is synthesized based on the meso‐functionalized ethoxy pillar[5]arene. Through the connectivity of two pillar[5]arenes by CC double bond, the central tetraphenylethylene (TPE) moiety is simultaneously formed. The resultant bicyclic molecule not only retains the host–guest properties of pillararenes but also introduces the interesting aggregation‐induced emission properties inherent in the embedded TPE structure. Three dinitrile derivatives with various linkers are designed as guests (G1, G2, and G3) to form host–guest assemblies with m‐TPE Di‐EtP5. The morphological control and fluorescence properties of the assemblies are successfully realized. G1 with a shorter alkyl chain as the linker completely threads into the cavities of the host. G2, due to its longer chain length, forms a linear supramolecular polymer upon binding to m‐TPE Di‐EtP5. G3 differs from G2 by possessing a bulky phenyl group in the middle of the chain, which can be further assembled with m‐TPE Di‐EtP5 to form supramolecular layered polymer and precipitated out in solution, and can be efficiently applied to photocatalytic reactions.
first_indexed 2024-04-09T21:53:18Z
format Article
id doaj.art-91bf7a3d21724437b1df6cd060215c99
institution Directory Open Access Journal
issn 2198-3844
language English
last_indexed 2024-04-09T21:53:18Z
publishDate 2023-03-01
publisher Wiley
record_format Article
series Advanced Science
spelling doaj.art-91bf7a3d21724437b1df6cd060215c992023-03-24T12:30:04ZengWileyAdvanced Science2198-38442023-03-01109n/an/a10.1002/advs.202206897Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic ApplicationsKaiya Wang0Rongbo Zhang1Zejing Song2Kaituo Zhang3Xueqi Tian4Srikala Pangannaya5Minzan Zuo6Xiao‐Yu Hu7College of Materials Science and Technology Nanjing University of Aeronautics and Astronautics Nanjing 211106 P. R. ChinaCollege of Materials Science and Technology Nanjing University of Aeronautics and Astronautics Nanjing 211106 P. R. ChinaCollege of Materials Science and Technology Nanjing University of Aeronautics and Astronautics Nanjing 211106 P. R. ChinaCollege of Materials Science and Technology Nanjing University of Aeronautics and Astronautics Nanjing 211106 P. R. ChinaCollege of Materials Science and Technology Nanjing University of Aeronautics and Astronautics Nanjing 211106 P. R. ChinaCollege of Materials Science and Technology Nanjing University of Aeronautics and Astronautics Nanjing 211106 P. R. ChinaCollege of Materials Science and Technology Nanjing University of Aeronautics and Astronautics Nanjing 211106 P. R. ChinaCollege of Materials Science and Technology Nanjing University of Aeronautics and Astronautics Nanjing 211106 P. R. ChinaAbstract A dimeric fluorescent macrocycle m‐TPE Di‐EtP5 (meso‐tetraphenylethylene dimeric ethoxypillar[5]arene) is synthesized based on the meso‐functionalized ethoxy pillar[5]arene. Through the connectivity of two pillar[5]arenes by CC double bond, the central tetraphenylethylene (TPE) moiety is simultaneously formed. The resultant bicyclic molecule not only retains the host–guest properties of pillararenes but also introduces the interesting aggregation‐induced emission properties inherent in the embedded TPE structure. Three dinitrile derivatives with various linkers are designed as guests (G1, G2, and G3) to form host–guest assemblies with m‐TPE Di‐EtP5. The morphological control and fluorescence properties of the assemblies are successfully realized. G1 with a shorter alkyl chain as the linker completely threads into the cavities of the host. G2, due to its longer chain length, forms a linear supramolecular polymer upon binding to m‐TPE Di‐EtP5. G3 differs from G2 by possessing a bulky phenyl group in the middle of the chain, which can be further assembled with m‐TPE Di‐EtP5 to form supramolecular layered polymer and precipitated out in solution, and can be efficiently applied to photocatalytic reactions.https://doi.org/10.1002/advs.202206897aggregation‐induced emissiondimeric pillar[5]arenephotocatalysissupramolecular assembly
spellingShingle Kaiya Wang
Rongbo Zhang
Zejing Song
Kaituo Zhang
Xueqi Tian
Srikala Pangannaya
Minzan Zuo
Xiao‐Yu Hu
Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic Applications
Advanced Science
aggregation‐induced emission
dimeric pillar[5]arene
photocatalysis
supramolecular assembly
title Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic Applications
title_full Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic Applications
title_fullStr Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic Applications
title_full_unstemmed Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic Applications
title_short Dimeric Pillar[5]arene as a Novel Fluorescent Host for Controllable Fabrication of Supramolecular Assemblies and Their Photocatalytic Applications
title_sort dimeric pillar 5 arene as a novel fluorescent host for controllable fabrication of supramolecular assemblies and their photocatalytic applications
topic aggregation‐induced emission
dimeric pillar[5]arene
photocatalysis
supramolecular assembly
url https://doi.org/10.1002/advs.202206897
work_keys_str_mv AT kaiyawang dimericpillar5areneasanovelfluorescenthostforcontrollablefabricationofsupramolecularassembliesandtheirphotocatalyticapplications
AT rongbozhang dimericpillar5areneasanovelfluorescenthostforcontrollablefabricationofsupramolecularassembliesandtheirphotocatalyticapplications
AT zejingsong dimericpillar5areneasanovelfluorescenthostforcontrollablefabricationofsupramolecularassembliesandtheirphotocatalyticapplications
AT kaituozhang dimericpillar5areneasanovelfluorescenthostforcontrollablefabricationofsupramolecularassembliesandtheirphotocatalyticapplications
AT xueqitian dimericpillar5areneasanovelfluorescenthostforcontrollablefabricationofsupramolecularassembliesandtheirphotocatalyticapplications
AT srikalapangannaya dimericpillar5areneasanovelfluorescenthostforcontrollablefabricationofsupramolecularassembliesandtheirphotocatalyticapplications
AT minzanzuo dimericpillar5areneasanovelfluorescenthostforcontrollablefabricationofsupramolecularassembliesandtheirphotocatalyticapplications
AT xiaoyuhu dimericpillar5areneasanovelfluorescenthostforcontrollablefabricationofsupramolecularassembliesandtheirphotocatalyticapplications