Conformationally switchable non-cyclic tetrapyrrole receptors: synthesis of tetrakis(1H-pyrrole-2-carbaldehyde) derivatives and their anion binding properties

被引：21

作者：

Deliomeroglu, Murat K. ^{[1
]}

Lynch, Vincent M. ^{[1
]}

Sessler, Jonathan L. ^{[1
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 80期

关键词：

D O I：

10.1039/c4cc05903d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A series of tetrakis(1H-pyrrole-2-carbaldehyde) receptors (2, 4, and 6) were synthesized in two steps from commercially available starting materials. The anion binding properties of these receptors can be tuned through electronic switching to stabilize a conformation displaying high affinity for the dihydrogenphosphate and pyrophosphate anions (as the tetrabutylammonium salts) in chloroform.

引用

页码：11863 / 11866

页数：4

共 15 条

[1] Quantification of Nitrate-π Interactions and Selective Transport of Nitrate Using Calix[4]pyrroles with Two Aromatic Walls [J].

Adriaenssens, Louis ;

Estarellas, Carolina ;

Jentzsch, Andreas Vargas ;

Martinez Belmonte, Marta ;

Matile, Stefan ;

Ballester, Pablo .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (22) :8324-8330

[2]

Anzenbacher P, 2000, J AM CHEM SOC, V122, P10268

[3] First cryptand-like calixpyrrole: Synthesis, X-ray structure, and anion binding properties of a bicyclic[3,3,3]nonapyrrole [J].

Bucher, C ;

Zimmerman, RS ;

Lynch, V ;

Sessler, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9716-9717

[4]

Connors A., 1987, Binding Constants: The Measurement of Molecular Complex Stability

[5] Calix[4]pyrroles: Old yet new anion-binding agents [J].

Gale, PA ;

Sessler, JL ;

Kral, V ;

Lynch, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (21) :5140-5141

[6] 2-amidopyrroles and 2,5-diamidopyrroles as simple anion binding agents [J].

Gale, PA ;

Camiolo, S ;

Tizzard, GJ ;

Chapman, CP ;

Light, ME ;

Coles, SJ ;

Hursthouse, MB .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23) :7849-7853

[7] Synthesis and anion binding studies of o-phenylenevinylene-bridged tetrapyrrolic macrocycle as an expanded analogue of calix[4]pyrrole [J].

Ghosh, Sudip Kumar ;

Ishida, Masatoshi ;

Li, Jiazhu ;

Cha, Won-Young ;

Lynch, Vincent M. ;

Kim, Dongho ;

Sessler, Jonathan L. .

CHEMICAL COMMUNICATIONS, 2014, 50 (28) :3753-3756

[8]

Jeffrey G.A., 1997, Topics in Physical Chemistry

[9] A scalable synthesis of meso-substituted dipyrromethanes [J].

Laha, JK ;

Dhanalekshmi, S ;

Taniguchi, M ;

Ambroise, A ;

Lindsey, JS .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (06) :799-812

[10] ONE-FLASK SYNTHESIS OF MESOSUBSTITUTED DIPYRROMETHANES AND THEIR APPLICATION IN THE SYNTHESIS OF TRANS-SUBSTITUTED PORPHYRIN BUILDING-BLOCKS [J].

LEE, CH ;

LINDSEY, JS .

TETRAHEDRON, 1994, 50 (39) :11427-11440

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