A general synthesis of macrocyclic π-electron-acceptor systems

Howard M. Colquhoun; Barnaby W. Greenland; Zhixue Zhu; John S. Shaw; Christine J. Cardin; Stefano Burattini; Joanne M. Elliott; Subhadeep Basu; Travis B. Gasa; J. Fraser Stoddart

doi:10.1021/ol9021782

A general synthesis of macrocyclic π-electron-acceptor systems

Howard M. Colquhoun, Barnaby W. Greenland, Zhixue Zhu, John S. Shaw, Christine J. Cardin, Stefano Burattini, Joanne M. Elliott, Subhadeep Basu, Travis B. Gasa, J. Fraser Stoddart

Chemistry

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20 Scopus citations

Abstract

Cyclocondensations of aromatic diamines with 1,1′-bis(2,4- dinitrophenyl)-4,4′-bipyridinium salts afford doubly or quadruply charged, macrocyclic, N,N′-diarylbipyridinium cations. These are tolerant of a wide range of acids, bases, and nucleophiles, although they appear to undergo reversible, one-electron reduction by tertiary amines. Single-crystal X-ray analysis demonstrates the presence of a macrocycle conformation in which the 4,4′-bipyridinium and 4,4′-biphenylenedisulfonyl residues are suitably spaced and aligned for complexation with .T-donor arenes, and NMR studies in solution indeed confirm binding to 1,5-bis[hydroxy(ethoxy)ethoxy] naphthalene.

Original language	English (US)
Pages (from-to)	5238-5241
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	22
DOIs	https://doi.org/10.1021/ol9021782
State	Published - 2009

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol9021782

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title = "A general synthesis of macrocyclic π-electron-acceptor systems",

abstract = "Cyclocondensations of aromatic diamines with 1,1′-bis(2,4- dinitrophenyl)-4,4′-bipyridinium salts afford doubly or quadruply charged, macrocyclic, N,N′-diarylbipyridinium cations. These are tolerant of a wide range of acids, bases, and nucleophiles, although they appear to undergo reversible, one-electron reduction by tertiary amines. Single-crystal X-ray analysis demonstrates the presence of a macrocycle conformation in which the 4,4′-bipyridinium and 4,4′-biphenylenedisulfonyl residues are suitably spaced and aligned for complexation with .T-donor arenes, and NMR studies in solution indeed confirm binding to 1,5-bis[hydroxy(ethoxy)ethoxy] naphthalene.",

author = "Colquhoun, {Howard M.} and Greenland, {Barnaby W.} and Zhixue Zhu and Shaw, {John S.} and Cardin, {Christine J.} and Stefano Burattini and Elliott, {Joanne M.} and Subhadeep Basu and Gasa, {Travis B.} and Stoddart, {J. Fraser}",

year = "2009",

doi = "10.1021/ol9021782",

language = "English (US)",

volume = "11",

pages = "5238--5241",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "22",

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TY - JOUR

T1 - A general synthesis of macrocyclic π-electron-acceptor systems

AU - Colquhoun, Howard M.

AU - Greenland, Barnaby W.

AU - Zhu, Zhixue

AU - Shaw, John S.

AU - Cardin, Christine J.

AU - Burattini, Stefano

AU - Elliott, Joanne M.

AU - Basu, Subhadeep

AU - Gasa, Travis B.

AU - Stoddart, J. Fraser

PY - 2009

Y1 - 2009

N2 - Cyclocondensations of aromatic diamines with 1,1′-bis(2,4- dinitrophenyl)-4,4′-bipyridinium salts afford doubly or quadruply charged, macrocyclic, N,N′-diarylbipyridinium cations. These are tolerant of a wide range of acids, bases, and nucleophiles, although they appear to undergo reversible, one-electron reduction by tertiary amines. Single-crystal X-ray analysis demonstrates the presence of a macrocycle conformation in which the 4,4′-bipyridinium and 4,4′-biphenylenedisulfonyl residues are suitably spaced and aligned for complexation with .T-donor arenes, and NMR studies in solution indeed confirm binding to 1,5-bis[hydroxy(ethoxy)ethoxy] naphthalene.

AB - Cyclocondensations of aromatic diamines with 1,1′-bis(2,4- dinitrophenyl)-4,4′-bipyridinium salts afford doubly or quadruply charged, macrocyclic, N,N′-diarylbipyridinium cations. These are tolerant of a wide range of acids, bases, and nucleophiles, although they appear to undergo reversible, one-electron reduction by tertiary amines. Single-crystal X-ray analysis demonstrates the presence of a macrocycle conformation in which the 4,4′-bipyridinium and 4,4′-biphenylenedisulfonyl residues are suitably spaced and aligned for complexation with .T-donor arenes, and NMR studies in solution indeed confirm binding to 1,5-bis[hydroxy(ethoxy)ethoxy] naphthalene.

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JF - Organic Letters

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ER -

A general synthesis of macrocyclic π-electron-acceptor systems

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CCDC 762943: Experimental Crystal Structure Determination

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A general synthesis of macrocyclic π-electron-acceptor systems

Abstract

ASJC Scopus subject areas

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CCDC 762943: Experimental Crystal Structure Determination

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