Colorimetric anion sensing by porphyrin-based anion receptors

被引：107

作者：

Lee, C ^{[1
]}

Lee, DH ^{[1
]}

Hong, JI ^{[1
]}

机构：

[1] Seoul Natl Univ, Coll Nat Sci, Sch Chem & Mol Engn, Seoul 151742, South Korea

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(01)01876-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Porphyrin derivatives 1-4 with H-bond donors and/or color-reporting chromophoric unit were synthesized and studied as anion-binding receptors. 1 and 2 exhibited binding selectivity in the order of AcO->H(2)PO(4)much greater than Cl-, Br-, I- in DMSO-d(6). Color change tests with several different anions for colorimetric anion sensors (3 and 4) resulted in selectivities for F-, AcO- and H2PO4- in organic solution. While 1 and 2 exhibited good selectivities for AcO- and H2PO4-, 3 and 4 showed a dramatic color change for F- due to increased interaction with a nitrophenylazo phenolic OH group. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8665 / 8668

页数：4

共 28 条

[11] RELATIVE BINDING-AFFINITY OF CARBOXYLATE AND ITS ISOSTERES - NITRO, PHOSPHATE, PHOSPHONATE, SULFONATE, AND DELTA-LACTONE [J].

KELLY, TR ;

KIM, MH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (16) :7072-7080

[12] Carbamate-appended Zn-porphyrin: a neutral receptor for anions [J].

Kim, YH ;

Hong, JI .

TETRAHEDRON LETTERS, 2000, 41 (22) :4419-4423

[13] Colorimetric chiral recognition by a molecular sensor [J].

Kubo, Y ;

Maeda, S ;

Tokita, S ;

Kubo, M .

NATURE, 1996, 382 (6591) :522-524

[14] CHIRAL AMINO-ACID RECOGNITION BY A PORPHYRIN-BASED ARTIFICIAL RECEPTOR [J].

KURODA, Y ;

KATO, Y ;

HIGASHIOJI, T ;

HASEGAWA, J ;

KAWANAMI, S ;

TAKAHASHI, M ;

SHIRAISHI, N ;

TANABE, K ;

OGOSHI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (44) :10950-10958

[15]

Lavigne JJ, 1999, ANGEW CHEM INT EDIT, V38, P3666, DOI 10.1002/(SICI)1521-3773(19991216)38:24<3666::AID-ANIE3666>3.0.CO

[16]

2-E

[17] Selective anion sensing based on a dual-chromophore approach [J].

Lee, DH ;

Lee, HY ;

Lee, KH ;

Hong, JI .

CHEMICAL COMMUNICATIONS, 2001, (13) :1188-1189

[18] An azophenol-based chromogenic anion sensor [J].

Lee, DH ;

Lee, KH ;

Hong, JI .

ORGANIC LETTERS, 2001, 3 (01) :5-8

[19] Fluoride-selective chromogenic sensors based on azophenol [J].

Lee, KH ;

Lee, HY ;

Lee, DH ;

Hong, JI .

TETRAHEDRON LETTERS, 2001, 42 (32) :5447-5449

[20] INCREASED YIELD OF A DESIRED ISOMER BY EQUILIBRIA DISPLACEMENT ON BINDING TO SILICA-GEL, APPLIED TO MESO-TETRAKIS(O-AMINOPHENYL)PORPHYRIN [J].

LINDSEY, J .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (25) :5215-5215

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