Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes

Flavio Picini; Susanne Schneider; Odile Gavat; Andreas Vargas Jentzsch; Junjun Tan; Mounir Maaloum; Jean-Marc Strub; Shoichi Tokunaga; Jean-Marie Lehn; Emilie Moulin; Nicolas Giuseppone

doi:10.1021/jacs.1c00623

Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes

Flavio Picini, Susanne Schneider, Odile Gavat, Andreas Vargas Jentzsch, Junjun Tan, Mounir Maaloum, Jean-Marc Strub, Shoichi Tokunaga, Jean-Marie Lehn^*, Emilie Moulin, Nicolas Giuseppone^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

37 Citations (Scopus)

Abstract

A S₆-symmetric triarylamine-based macrocycle (i.e., hexaaza[1₆]paracyclophane), decorated with six lateral amide functions, is synthesized by a convergent and modular strategy. This macrocycle is shown to undergo supramolecular polymerization in o-dichlorobenzene, and its nanotubular structure is elucidated by a combination of spectroscopy and microscopy techniques, together with X-ray scattering and molecular modeling. Upon sequential oxidation, a spectroelectrochemical analysis of the supramolecular polymer suggests an extended electronic delocalization of charge carriers both within the macrocycles (through bond) and between the macrocycles along the stacking direction (through space).

Original language	English
Pages (from-to)	6498-6504
Journal	Journal of the American Chemical Society
Volume	143
Issue number	17
Online published	9 Apr 2021
DOIs	https://doi.org/10.1021/jacs.1c00623
Publication status	Published - 5 May 2021
Externally published	Yes

Access Output

10.1021/jacs.1c00623

Other Access Options

Check CityUHK Library

Permanent Link

Right click to copy link

Cite this

@article{7e75f8b3de894bd583d2f674e736f3f0,

title = "Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes",

abstract = "A S6-symmetric triarylamine-based macrocycle (i.e., hexaaza[16]paracyclophane), decorated with six lateral amide functions, is synthesized by a convergent and modular strategy. This macrocycle is shown to undergo supramolecular polymerization in o-dichlorobenzene, and its nanotubular structure is elucidated by a combination of spectroscopy and microscopy techniques, together with X-ray scattering and molecular modeling. Upon sequential oxidation, a spectroelectrochemical analysis of the supramolecular polymer suggests an extended electronic delocalization of charge carriers both within the macrocycles (through bond) and between the macrocycles along the stacking direction (through space).",

author = "Flavio Picini and Susanne Schneider and Odile Gavat and {Vargas Jentzsch}, Andreas and Junjun Tan and Mounir Maaloum and Jean-Marc Strub and Shoichi Tokunaga and Jean-Marie Lehn and Emilie Moulin and Nicolas Giuseppone",

year = "2021",

month = may,

day = "5",

doi = "10.1021/jacs.1c00623",

language = "English",

volume = "143",

pages = "6498--6504",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes

AU - Picini, Flavio

AU - Schneider, Susanne

AU - Gavat, Odile

AU - Vargas Jentzsch, Andreas

AU - Tan, Junjun

AU - Maaloum, Mounir

AU - Strub, Jean-Marc

AU - Tokunaga, Shoichi

AU - Lehn, Jean-Marie

AU - Moulin, Emilie

AU - Giuseppone, Nicolas

PY - 2021/5/5

Y1 - 2021/5/5

N2 - A S6-symmetric triarylamine-based macrocycle (i.e., hexaaza[16]paracyclophane), decorated with six lateral amide functions, is synthesized by a convergent and modular strategy. This macrocycle is shown to undergo supramolecular polymerization in o-dichlorobenzene, and its nanotubular structure is elucidated by a combination of spectroscopy and microscopy techniques, together with X-ray scattering and molecular modeling. Upon sequential oxidation, a spectroelectrochemical analysis of the supramolecular polymer suggests an extended electronic delocalization of charge carriers both within the macrocycles (through bond) and between the macrocycles along the stacking direction (through space).

AB - A S6-symmetric triarylamine-based macrocycle (i.e., hexaaza[16]paracyclophane), decorated with six lateral amide functions, is synthesized by a convergent and modular strategy. This macrocycle is shown to undergo supramolecular polymerization in o-dichlorobenzene, and its nanotubular structure is elucidated by a combination of spectroscopy and microscopy techniques, together with X-ray scattering and molecular modeling. Upon sequential oxidation, a spectroelectrochemical analysis of the supramolecular polymer suggests an extended electronic delocalization of charge carriers both within the macrocycles (through bond) and between the macrocycles along the stacking direction (through space).

UR - http://www.scopus.com/inward/record.url?scp=85105065829&partnerID=8YFLogxK

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85105065829&origin=recordpage

U2 - 10.1021/jacs.1c00623

DO - 10.1021/jacs.1c00623

M3 - RGC 21 - Publication in refereed journal

C2 - 33834779

SN - 0002-7863

VL - 143

SP - 6498

EP - 6504

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 17

ER -

Supramolecular Polymerization of Triarylamine-Based Macrocycles into Electroactive Nanotubes

Abstract

Access Output

Other Access Options

Permanent Link

Other Files and Links

Fingerprint

Cite this