1,8-Diamino-3,6-dichlorocarbazole:  A Promising Building Block for Anion Receptors

Chmielewski, Michał J.; Charon, Michał; Jurczak, Janusz

doi:10.1021/ol048661e

Cited by 172 publications

(103 citation statements)

References 18 publications

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“…[8] The preparation included selective chlorination of the carbazole hydrocarbon in positions 3 and 6 (the most reactive positions of the molecule) followed by nitration in positions 1 and 8 of the carbazole framework. The obtained nitro-derivative was reduced in the atmosphere of hydrogen with 10 % Pd/C as a catalyst, yielding the carbazole amine 1.…”

Section: Resultsmentioning

confidence: 99%

“…Anion binding has been reported for the derivatives of amidopyrroles, [4] calixpyrrole, [5] porphyrines, [6] as well as dipyrromethanes. [7] After Jurczak et al [8] showed that the rigid π-conjugated skeleton of carbazole allows an easy introduction of various functionalities, the carbazole molecule became an ideal moiety for the design of efficient anion receptors. [9] Carbazole also has the polarized NH hydrogen which can form the H-bond with anions.…”

Section: Introductionmentioning

confidence: 99%

“…Additionally, carbazole derivatives are often colored which enables their spectrophotometric detection. [10] Many anion receptors containing the carbazole backbone have been prepared, [8,11] some of them also in combination with the pyrrole moiety. [9,12] On the other hand, the examples of carbazole Schiff-base anion receptors are very rare in the literature.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Anion Binding Properties of a Novel 1,8-dipyrrolecarbazole Schiff-base

Šekutor¹,

Opačak²,

Alešković³

et al. 2015

Croat. Chem. Acta

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New anion receptor N 1 ,N 8 -bis[1H-pyrro-2-yl-methylidene]-3,6-dichloro-9H-carbazole-1,8-diamine (3) was synthesized and its binding properties towards anions (Cl -, Br -, AcO -and H2PO4 -) investigated by UV/Vis spectroscopy. In order to find the most stable structure of receptor 3, geometries of all possible isomers of 3 were optimized by the DFT/B3LYP method. It has been determined that receptor 3 forms complexes with a 1:1 stoichiometry with all the studied anions and no significant selectivity with respect to anion geometry was found. However, 1,8-dipyrrolecarbazole Schiff-base 3 binds oxoanions (H2PO4 -and AcO -) more strongly than spherical halogenide (Cl -and Br -) anions.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Anion Binding Properties of a Novel 1,8-dipyrrolecarbazole Schiff-base

Šekutor¹,

Opačak²,

Alešković³

et al. 2015

Croat. Chem. Acta

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“…[39][40][41][42][43] For these considerations, many synthetic approaches have been developed towards the syntheses of aminocarbazoles and their derivatives. [44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59] Aryl and heteroaryl-annulated carbazoles, such as pyridocarbazoles, indolocarbazoles, and pyrrolocarbazoles have attracted growing attention since they are distributed in numerous natural products with diverse useful bioactivities. [60][61][62][63][64][65][66][67][68] Aminocarbazoles have been an important synthon to construct pyridocarbazoles, 69 which are well known for their antitumor properties.…”

Section: Introductionmentioning

confidence: 99%

Applications of aminocarbazoles in heterocyclic synthesis

Reddy¹,

Padmaja²

2015

Arkivoc

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Aminocarbazoles are versatile building blocks in organic synthesis. This review focuses on the application of aminocarbazoles to generate a large variety of fused carbazole heterocycles such as pyridocarbazoles, isomeric pyridocarbazoles, thiazolocarbazoles, pyrimidocarbazoles, pyrrolocarbazoles, indolocarbazoles, quino-and chromeno-carbazoles and many others. Many of these molecules exhibit promising biological activities.

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“…[20][21][22][23][24][25][26][27] However, C-H…anion hydrogen bonds play an important role in nature.…”

Section: Introductionmentioning

confidence: 99%

Dihydrogen Phosphate Selective Anion Receptor Based on Acylhydrazone

Pandian¹,

Kang

2014

Bulletin of the Korean Chemical Society

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Anion receptor 1 based on acylhydrazone has been designed and synthesized. UV-vis and 1 H NMR titration showed that receptor 1 is selective receptor for dihydrogen phosphate (H2PO4 − ). Dihydrogen phosphate was complexed by the receptor 1 via at least 4 hydrogen bonding interactions, contributing from two amide N-Hs and two imine C-Hs. In addition, nitrogen in the aromatic ring could make 2 additional hydrogen bondings with OH groups in the dihydrogen phosphate. However, the receptor 1 could make only 4 hydrogen bonds with halides. Therefore, receptor 1 could bind anions through hydrogen bonds with a selectivity in the order of H2PO4 − > Br − > Cl − in highly polar solvent such as DMSO.

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1,8-Diamino-3,6-dichlorocarbazole: A Promising Building Block for Anion Receptors

Abstract: [reaction: see text] Advantages of the carbazole moiety as a new skeleton for the construction of anion receptors are illustrated by two model amide receptors derived from 1,8-diamino-3,6-dichlorocarbazole.

Cited by 172 publications

References 18 publications

Synthesis and Anion Binding Properties of a Novel 1,8-dipyrrolecarbazole Schiff-base

Synthesis and Anion Binding Properties of a Novel 1,8-dipyrrolecarbazole Schiff-base

Applications of aminocarbazoles in heterocyclic synthesis

Dihydrogen Phosphate Selective Anion Receptor Based on Acylhydrazone

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