Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives

Maleki, Behrooz; Salehabadi, Hafezeh

doi:10.5155/eurjchem.1.4.377-380.165

Cited by 41 publications

(13 citation statements)

References 36 publications

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“…10 The Suzuki cross-coupling reaction of benzothiazoles 1a-1c with 4-(1,2,2-triphenylvinyl)phenylboronic acid pinacol ester (2) using Pd(PPh 3 ) 4 as a catalyst resulted 3a-3c in 67%, 78% and 66% yields respectively. The bromo-benzothiazoles 1a-1c were synthesized by the condensation reaction of 2-amino thiophenol and (ortho/meta/para)bromobenzaldehyde respectively in the presence of ammonium chloride and acetic acid.…”

Section: Resultsmentioning

confidence: 99%

Mechanochromism and aggregation induced emission in benzothiazole substituted tetraphenylethylenes: a structure function correlation

et al. 2015

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The donor-acceptor benzothiazole substituted tetraphenylethylenes (BT-TPEs) 3a-3c were designed and synthesized to examine the effect of the linkage between the BT and the TPE unit on the photophysical, aggregation induced emission (AIE) and mechanochromic properties. The syntheses of BT-TPEs 3a-3cwere achieved by the Pd-catalyzed Suzuki cross-coupling reaction of bromobenzothiazoles 1a-1c with 4-(1,2,2-triphenylvinyl)phenylboronic acid pinacol ester (2). The study showed that their photophysical, AIE and mechanochromic properties are dependent on the linkage between the BT and the TPE unit (ortho, meta, and para). The meta isomer 3b shows the highest grinding induced spectral shift (51 nm) whereas the ortho isomer 3a shows the lowest grinding induced spectral shift (9 nm). The single crystal X-ray structures reveal the highly twisted conformation and tight packing in BT-TPE 3a compared to 3b.The thermogravimetric analysis of BT-TPEs shows good thermal stability. The computational study reveals the donor-acceptor nature of the BT-TPEs. The structure-function correlation indicates that the mechanochromic and aggregation induced emission (AIE) properties were dependent on the linkage between BT and TPE. † Electronic supplementary information (ESI) available: Experimental procedures, NMR spectra, UV-vis spectra, mechanochromic effect, computational data and crystal structural data for 3a and 3b. CCDC 1044876 and 1044877. For ESI and crystallographic data in CIF or other electronic format see Scheme 1 Synthesis of BT-TPEs 3a-3c. Fig. 1 Fluorescence spectra of (a) 3a, (b) 3b and (c) 3c in THF-water mixtures with different water fractions (10 mM). (d) Fluorescence quantum yields of the BT-TPEs in water-THF mixtures against different volume fractions of water.This journal is

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Section: Resultsmentioning

confidence: 99%

Mechanochromism and aggregation induced emission in benzothiazole substituted tetraphenylethylenes: a structure function correlation

et al. 2015

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“…They also prepared the halogen bonded co-crystal 78. By referring to the previous report by Bushuyev et al, 33 they synthesized compound 76 by iodination of tetrauoroaniline (75) in the presence of iodine (I 2 ) and (78) were formed, mainly due to C-I/NPy interactions. Furthermore, the authors prepared the hydrogen bonded complexes 79a-g by dissolving compound 77 and 4-alkoxystilbazoles in THF followed by slow evaporation of the solvent and drying under vacuum.…”

Section: Pyridine-based Molecules As Thermotropic Mesogensmentioning

confidence: 99%

“…2-(pyridin-4-yl)benzothiazole (190), was synthesized by an altered strategy based on the previous literature report by Maleki and Salehabadi. 78 According to this procedure, the o-amino thiophenol (188), aldehyde (189), and ammonium chloride catalyst were reuxed in ethanol solvent. On the other hand, the hydrogen donors, i.e.…”

Section: Pyridine-based Molecules As Thermotropic Mesogensmentioning

confidence: 99%

Recent synthetic advances in pyridine-based thermotropic mesogens

Devadiga

Ahipa

2019

RSC Adv.

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“…30 The reaction stopped at the benzothiazoline derivative when carried out under nitrogen atmosphere thus proving that aerial oxygen is absolutely essential for the oxidation step.…”

Section: Viiiii Synthesis Of Arylbenzothiazoles and Bisbenzothiazolesmentioning

confidence: 99%

Recent progress of Ammonium chloride as catalyst in organic synthesis

Pal¹

2013

IOSR-JAC

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Ammonium chloride; as a mild and efficient catalyst for the synthesis of some 2-arylbenzothiazoles and bisbenzothiazole derivatives

Cited by 41 publications

References 36 publications

Mechanochromism and aggregation induced emission in benzothiazole substituted tetraphenylethylenes: a structure function correlation

Mechanochromism and aggregation induced emission in benzothiazole substituted tetraphenylethylenes: a structure function correlation

Recent synthetic advances in pyridine-based thermotropic mesogens

Recent progress of Ammonium chloride as catalyst in organic synthesis

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