2016
DOI: 10.1002/slct.201600238
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Cholesterol–based Bisamides on Biphenyl Backbone: A Case of Selective Visual Sensing of F and H2PO4 through Breaking and Making of Gels

Abstract: Cholesterol linked bisamides 1–3 on biphenyl spacers have been designed and synthesized. Compound 1 forms gel in CHCl3 – n‐hexane (1:6, v/v) solvent and the gel is selectively collapsed into sol in presence of F− with a color change from yellowish white to greenish yellow. Presence of pyridinium amides in 2 and 3 showed different gelation behaviours. While the chloride salt 2 displayed gelation in CHCl3 in presence of H2PO4−, compound 3 formed gel in DMSO: H2O (1:2, v/v) without having any assistance of extern… Show more

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Cited by 15 publications
(6 citation statements)
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“…Compound 1 was synthesised according to the Scheme . Initially cholesterol was converted to the chloride 2 which on coupling with 4‐hydroxybenzaldehyde in the presence of K 2 CO 3 in CH 3 CN under refluxing condition introduced the compound 3 . Oxidative condensation between o ‐phenylenediamine and aldehyde 3 in dry DMSO at 90 °C afforded compound 1 in appreciable yield.…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Compound 1 was synthesised according to the Scheme . Initially cholesterol was converted to the chloride 2 which on coupling with 4‐hydroxybenzaldehyde in the presence of K 2 CO 3 in CH 3 CN under refluxing condition introduced the compound 3 . Oxidative condensation between o ‐phenylenediamine and aldehyde 3 in dry DMSO at 90 °C afforded compound 1 in appreciable yield.…”
Section: Resultsmentioning
confidence: 99%
“…During our ongoing effort in the area of supramolecular chemistry research, we have used the different simple heterocylic motifs (e. g., pyridinium,, benzimidazolium and benzimidazole, triazole etc.) in devising some useful molecular sensors for ionic substrates.…”
Section: Introductionmentioning
confidence: 99%
“…Compounds 1 and 2 were achieved according to the Scheme . Initially, cholesterol was converted to the chloride 3 which on coupling with 4‐hydroxybenzaldehyde in the presence of K 2 CO 3 in CH 3 CN under refluxing condition gave the compound 4 . Oxidative condensation of 1,2‐diaminoanthraquinone with the aldehyde 4 and 4‐hydroxybenzaldehyde in EtOH containing 4 drops of trifluoroacetic acid (TFA) at 90 °C afforded compounds 1 and 2 , respectively in appreciable yields.…”
Section: Resultsmentioning
confidence: 99%
“…Compounds 1–9 were obtained according to Scheme . Cholesterol was initially converted to chloride 10 . The reaction of benzimidazole separately with m -xylene dibromide, benzyl bromide, 9-chloromethyl anthracene, and n -butyl bromide in the presence of NaH in dry tetrahydrofuran (THF) afforded compounds 11 , 12 , 13 , and 14 , respectively.…”
Section: Resultsmentioning
confidence: 99%
“…Our ongoing interest in the synthesis of stimuli-responsive cholesterol-based supramolecular gelators , has inspired us to report herein the synthesis and gelation behavior of a series of structurally diversed cholesterol-appended benzimidazolium compounds 1–9 (Figure ). The gelation of the benzimidazolium salts is dependent on the nature of the counteranion.…”
Section: Introductionmentioning
confidence: 99%