“Rim-Differentiated” Pillar[6]arenes

Yang Chao; Tushar Ulhas Thikekar; Wangjian Fang; Rong Chang; Jiong Xu; Nianfeng Ouyang; Jun Xu; Yan Gao; Minjie Guo; Han Zuilhof; Andrew C.H. Sue

doi:10.1002/anie.202204589

“Rim-Differentiated” Pillar[6]arenes

Yang Chao, Tushar Ulhas Thikekar, Wangjian Fang, Rong Chang, Jiong Xu, Nianfeng Ouyang, Jun Xu, Yan Gao, Minjie Guo, Han Zuilhof, Andrew C.H. Sue^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

26 Citations (Scopus)

Abstract

A “rim-differentiated” pillar[6]arene (RD-P[6]) was obtained successfully, with the assistance of a dimeric silver trifluoroacetate template, among eight different constitutional isomers in a direct and regioselective manner. The solid-state conformation of this macrocycle could switch from the 1,3,5-alternate to a truly rim-differentiated one upon guest inclusion. This highly symmetric RD-P[6] not only hosts metal-containing molecules inside its cavity, but also can form a pillar[6]arene-C₆₀ adduct through co-crystallization on account of donor-acceptor interactions. The development of synthetic strategies to desymmetrize pillararenes offers new opportunities for engineering complex molecular architectures and organic electronic materials.

Original language	English
Journal	Angewandte Chemie - International Edition
Volume	61
Issue number	31
Early online date	22 Apr 2022
DOIs	https://doi.org/10.1002/anie.202204589
Publication status	Published - Aug 2022

Keywords

Co-Crystals
Host–Guest Chemistry
Macrocycles
Pillar[n]arenes
Tiara[n]arenes

Access to Document

10.1002/anie.202204589

CCDC 2073870: Experimental Crystal Structure Determination
Chao, Y. (Creator), Thikekar, T. U. (Creator), Fang, W. (Creator), Chang, R. (Creator), Xu, J. (Creator), Ouyang, N. (Creator), Xu, J. (Creator), Gao, Y. (Creator), Guo, M. (Creator), Zuilhof, H. (Creator) & Sue, A. C. H. (Creator), Wageningen University & Research, 29 Mar 2021
DOI: 10.5517/ccdc.csd.cc27m11z
Dataset
CCDC 2073865: Experimental Crystal Structure Determination
Chao, Y. (Creator), Thikekar, T. U. (Creator), Fang, W. (Creator), Chang, R. (Creator), Xu, J. (Creator), Ouyang, N. (Creator), Xu, J. (Creator), Gao, Y. (Creator), Guo, M. (Creator), Zuilhof, H. (Creator) & Sue, A. C. H. (Creator), Tianjin University, 29 Mar 2021
DOI: 10.5517/ccdc.csd.cc27m0ws
Dataset
CCDC 2073967: Experimental Crystal Structure Determination
Chao, Y. (Creator), Thikekar, T. U. (Creator), Fang, W. (Creator), Chang, R. (Creator), Xu, J. (Creator), Ouyang, N. (Creator), Xu, J. (Creator), Gao, Y. (Creator), Guo, M. (Creator), Zuilhof, H. (Creator) & Sue, A. C. H. (Creator), Tianjin University, 29 Mar 2021
DOI: 10.5517/ccdc.csd.cc27m456
Dataset

Cite this

@article{bc6ec40cbbca466ab311d2b7dde1cd82,

title = "“Rim-Differentiated” Pillar[6]arenes",

abstract = "A “rim-differentiated” pillar[6]arene (RD-P[6]) was obtained successfully, with the assistance of a dimeric silver trifluoroacetate template, among eight different constitutional isomers in a direct and regioselective manner. The solid-state conformation of this macrocycle could switch from the 1,3,5-alternate to a truly rim-differentiated one upon guest inclusion. This highly symmetric RD-P[6] not only hosts metal-containing molecules inside its cavity, but also can form a pillar[6]arene-C60 adduct through co-crystallization on account of donor-acceptor interactions. The development of synthetic strategies to desymmetrize pillararenes offers new opportunities for engineering complex molecular architectures and organic electronic materials.",

keywords = "Co-Crystals, Host–Guest Chemistry, Macrocycles, Pillar[n]arenes, Tiara[n]arenes",

author = "Yang Chao and Thikekar, {Tushar Ulhas} and Wangjian Fang and Rong Chang and Jiong Xu and Nianfeng Ouyang and Jun Xu and Yan Gao and Minjie Guo and Han Zuilhof and Sue, {Andrew C.H.}",

year = "2022",

month = aug,

doi = "10.1002/anie.202204589",

language = "English",

volume = "61",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

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number = "31",

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TY - JOUR

T1 - “Rim-Differentiated” Pillar[6]arenes

AU - Chao, Yang

AU - Thikekar, Tushar Ulhas

AU - Fang, Wangjian

AU - Chang, Rong

AU - Xu, Jiong

AU - Ouyang, Nianfeng

AU - Xu, Jun

AU - Gao, Yan

AU - Guo, Minjie

AU - Zuilhof, Han

AU - Sue, Andrew C.H.

PY - 2022/8

Y1 - 2022/8

N2 - A “rim-differentiated” pillar[6]arene (RD-P[6]) was obtained successfully, with the assistance of a dimeric silver trifluoroacetate template, among eight different constitutional isomers in a direct and regioselective manner. The solid-state conformation of this macrocycle could switch from the 1,3,5-alternate to a truly rim-differentiated one upon guest inclusion. This highly symmetric RD-P[6] not only hosts metal-containing molecules inside its cavity, but also can form a pillar[6]arene-C60 adduct through co-crystallization on account of donor-acceptor interactions. The development of synthetic strategies to desymmetrize pillararenes offers new opportunities for engineering complex molecular architectures and organic electronic materials.

AB - A “rim-differentiated” pillar[6]arene (RD-P[6]) was obtained successfully, with the assistance of a dimeric silver trifluoroacetate template, among eight different constitutional isomers in a direct and regioselective manner. The solid-state conformation of this macrocycle could switch from the 1,3,5-alternate to a truly rim-differentiated one upon guest inclusion. This highly symmetric RD-P[6] not only hosts metal-containing molecules inside its cavity, but also can form a pillar[6]arene-C60 adduct through co-crystallization on account of donor-acceptor interactions. The development of synthetic strategies to desymmetrize pillararenes offers new opportunities for engineering complex molecular architectures and organic electronic materials.

KW - Co-Crystals

KW - Host–Guest Chemistry

KW - Macrocycles

KW - Pillar[n]arenes

KW - Tiara[n]arenes

U2 - 10.1002/anie.202204589

DO - 10.1002/anie.202204589

M3 - Article

AN - SCOPUS:85129264047

SN - 1433-7851

VL - 61

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 31

ER -

“Rim-Differentiated” Pillar[6]arenes

Abstract

Keywords

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Datasets

CCDC 2073870: Experimental Crystal Structure Determination

CCDC 2073865: Experimental Crystal Structure Determination

CCDC 2073967: Experimental Crystal Structure Determination

Cite this