Cyclo[m]pyridine[n]pyrroles: Hybrid macrocycles that display expanded π-conjugation upon protonation

Zhan Zhang; Jong Min Lim; Masatoshi Ishida; Vladimir V. Roznyatovskiy; Vincent M. Lynch; Han Yuan Gong; Xiaoping Yang; Dongho Kim; Jonathan L. Sessler

doi:10.1021/ja211985k

Cyclo[m]pyridine[n]pyrroles: Hybrid macrocycles that display expanded π-conjugation upon protonation

Zhan Zhang, Jong Min Lim, Masatoshi Ishida, Vladimir V. Roznyatovskiy, Vincent M. Lynch, Han Yuan Gong, Xiaoping Yang, Dongho Kim, Jonathan L. Sessler

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

74 Scopus citations

Abstract

Novel hybrid cyclo[m]pyridine[n]pyrroles have been synthesized using Suzuki coupling. Their NMR and optical spectroscopic features and solid state structural parameters provide support for the proposal that these species are best described as locally aromatic compounds devoid of long-range intersubunit conjugation. However, an extension of the π-conjugation in the macrocycles can be realized through protonation, as inferred from optical spectroscopic and X-ray diffraction-based structural studies.

Original language	English
Pages (from-to)	4076-4079
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	134
Issue number	9
DOIs	https://doi.org/10.1021/ja211985k
State	Published - 7 Mar 2012

Access to Document

10.1021/ja211985k

Cite this

@article{aa160bf61c4648888ab77cf208e3e8ec,

title = "Cyclo[m]pyridine[n]pyrroles: Hybrid macrocycles that display expanded π-conjugation upon protonation",

abstract = "Novel hybrid cyclo[m]pyridine[n]pyrroles have been synthesized using Suzuki coupling. Their NMR and optical spectroscopic features and solid state structural parameters provide support for the proposal that these species are best described as locally aromatic compounds devoid of long-range intersubunit conjugation. However, an extension of the π-conjugation in the macrocycles can be realized through protonation, as inferred from optical spectroscopic and X-ray diffraction-based structural studies.",

author = "Zhan Zhang and Lim, {Jong Min} and Masatoshi Ishida and Roznyatovskiy, {Vladimir V.} and Lynch, {Vincent M.} and Gong, {Han Yuan} and Xiaoping Yang and Dongho Kim and Sessler, {Jonathan L.}",

year = "2012",

month = mar,

day = "7",

doi = "10.1021/ja211985k",

language = "English",

volume = "134",

pages = "4076--4079",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "9",

}

TY - JOUR

T1 - Cyclo[m]pyridine[n]pyrroles

T2 - Hybrid macrocycles that display expanded π-conjugation upon protonation

AU - Zhang, Zhan

AU - Lim, Jong Min

AU - Ishida, Masatoshi

AU - Roznyatovskiy, Vladimir V.

AU - Lynch, Vincent M.

AU - Gong, Han Yuan

AU - Yang, Xiaoping

AU - Kim, Dongho

AU - Sessler, Jonathan L.

PY - 2012/3/7

Y1 - 2012/3/7

N2 - Novel hybrid cyclo[m]pyridine[n]pyrroles have been synthesized using Suzuki coupling. Their NMR and optical spectroscopic features and solid state structural parameters provide support for the proposal that these species are best described as locally aromatic compounds devoid of long-range intersubunit conjugation. However, an extension of the π-conjugation in the macrocycles can be realized through protonation, as inferred from optical spectroscopic and X-ray diffraction-based structural studies.

AB - Novel hybrid cyclo[m]pyridine[n]pyrroles have been synthesized using Suzuki coupling. Their NMR and optical spectroscopic features and solid state structural parameters provide support for the proposal that these species are best described as locally aromatic compounds devoid of long-range intersubunit conjugation. However, an extension of the π-conjugation in the macrocycles can be realized through protonation, as inferred from optical spectroscopic and X-ray diffraction-based structural studies.

UR - http://www.scopus.com/inward/record.url?scp=84863230536&partnerID=8YFLogxK

U2 - 10.1021/ja211985k

DO - 10.1021/ja211985k

M3 - Article

C2 - 22332703

AN - SCOPUS:84863230536

SN - 0002-7863

VL - 134

SP - 4076

EP - 4079

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 9

ER -

Cyclo[m]pyridine[n]pyrroles: Hybrid macrocycles that display expanded π-conjugation upon protonation

Abstract

Access to Document

Other files and links

Fingerprint

Cite this