3464-50-4Relevant articles and documents
Calix[4]resorcinarene-cholesterol columnar liquid crystals: Synthesis, mesomorphism and the influence of spacers on liquid crystalline behaviors
Han, Chenyang,Guo, Hongyu,Lai, Jianbin,Yang, Fafu
, p. 220 - 224 (2017)
Novel calix[4]resorcinarene derivatives with four cholesterol units bridging by soft spacers or rigid Schiff-base spacers were prepared in yields of 63–76%. The hexagonal columnar liquid crystalline behaviors were firstly observed for calix[4]resorcinarene derivatives. The mesomorphic properties were influenced greatly by the structures of spacers. The rigid spacers were favorable for enhancing the phase transition temperatures and enlarging the temperature scopes of mesophase.
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van der Molen,H.J. et al.
, p. 195 - 214 (1965)
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Coumarin-based supramolecular gelator: A case of selective detection of F- and HP2O73-
Ghosh, Kumaresh,Panja, Santanu
, p. 12094 - 12099 (2015)
Coumarin appended 1,2,3-triazole coupled cholesterol 1 which acts as a small molecular gelator has been designed and synthesized. Compound 1 has been noted to form gel from CHCl3-petroleum ether (1: 1, v/v). The stable gel is anion responsive. The gel state is transformed into the sol state selectively in the presence of F- and hydrogen pyrophosphate and thus validates their visual sensing over a series of other anions. Fluorescence study in CH3CN containing 0.5% DMSO also reveals substantial change in emission of 1 upon addition of both F- and hydrogen pyrophosphate and distinguishes them from other anions studied.
Cholesterol linked benzothiazole: A versatile gelator for detection of picric acid and metal ions such as Ag+, Hg2+, Fe3+ and Al3+ under different conditions
Mondal, Subhendu,Raza, Rameez,Ghosh, Kumaresh
, p. 10509 - 10516 (2019)
Cholesterol-appended benzothiazole 1 has been designed and synthesized. Compound 1 exhibits gelation in different solvents. The benzothiazole and cholesteryl motifs play a pivotal role in aggregation in organic solvents involving π-stacking and hydrophobic interactions, respectively. As an application, the nitrobenzene gel with good rheological properties has been noted to be useful in molecular recognition studies of multiple analytes ranging from neutral to ionic in nature. It selectively recognizes picric acid (PA) over a series of nitroaromatics by exhibiting a gel-to-sol phase transition with a distinguishable color change from pale yellow to deep yellow. On the other hand, the nitrobenzene gel shows selective recognition potential for Ag+ and Hg2+ ions through a gel-to-sol phase transition and the cations are distinguished by F-. The gelator 1 also reveals a measurable selective interaction with picric acid over a series of nitroaromatics in CH3CN containing 1% CHCl3. In CH3CN containing 1% CHCl3, compound 1 further shows affinity towards Fe3+, Al3+ and Hg2+ with distinctive features.
Cholesterol-Appended Benzimidazolium Salts: Synthesis, Aggregation, Sensing, Dye Adsorption, and Semiconducting Properties
Panja, Santanu,Bhattacharya, Subhratanu,Ghosh, Kumaresh
, p. 8277 - 8288 (2017)
A series of cholesterol-appended benzimidazolium salts 1-9 have been designed and synthesized. They have been explored in gel chemistry. The gelation of the benzimidazolium salts is dependent on the nature of the counteranions. In addition, the gelation behavior of the gelators is linked with the presence of both π-stacking and cholesteryl motifs. Whereas bisbenzimidazolium salt 2 forms a gel in dimethylsulfoxide/H2O (1:1, v/v) itself, under similar conditions, monobenzimidazolium salts 4 and 6 exhibit gelation in the presence of F- ions and validate the visual sensing of F-. As an application, the gel phase of 2 efficiently removes toxic dyes from waste water. Furthermore, all gels show thermally activated semiconducting property within a wide voltage window.
A novel cholesterol conjugated fluorescence probe for Cu2+ detection and bioimaging in living cells
Ting, Jia,Mei, Fu,Mengyao, Zhang,Jianwen, Qiu,Hu, Zhu,Yong, Gao
, (2020)
A cholesterol conjugated fluorescence probe T was designed and synthesized. The probe T can be used for recognition of Cu2+ by the absorption spectrum, fluorescence spectrum, and naked eyes respectively in aqueous solution. The cell imaging experiments showed that the probe has good membrane permeability and a huge potentiality for the detection of Cu2+ in living cells.
Ion conducting cholesterol appended pyridinium bisamide-based gel for the selective detection of Ag+ and Cl- ions
Ghosh, Kumaresh,Kar, Debasis,Panja, Santanu,Bhattacharya, Subhratanu
, p. 3798 - 3803 (2014)
Cholesterol appended bispyridinium isophthalamide dichloride (1) has been designed and synthesized. While compound 1 forms a gel in CHCl3, the cholesterol appended bispyridinium isophthalamide dihexafluorophosphate (1a) analogue that results from 1 on anion exchange does not form a gel in any solvent combination. The chloroform gel of 1 is pH responsive and shows thermally activated ionic conductivity. It serves as a medium for the specific detection of Ag+ ions over a series of examined cations. Compound 1a, on the other hand, acts as a selective Cl- ion detector by forming a gel in chloroform in the presence of tetrabutylammonium chloride.
Cholesteryl-containing ionic liquid crystals composed of alkylimidazolium cations and different anions
Lan, Xin,Bai, Lu,Li, Xin,Ma, Shuang,He, Xiaozhi,Meng, Fanbao
, p. 515 - 524 (2014)
Cholesteryl-containing ionic liquid crystals (ILCs) 1-cholesteryloxycarbonylmethyl(propyl)-3-methyl(butyl)imidazolium chlorides ([Ca-Me-Im]Cl, [Ca-Bu-Im]Cl, [Cb-Me-Im]Cl and [Cb-Bu-Im]Cl) and corresponding imidazolium tetrachloroaluminates ([Ca-Me-Im]AlCl4, [Ca-Bu-Im]AlCl4, [Cb-Me-Im]AlCl4 and [Cb-Bu-Im]AlCl4) were synthesized in this work, and the chemical structure, LC behavior and ionic conductivity of all these ILCs were characterized by several technical methods. The imidazolium-based salts with Cl- ions showed chiral smectic A (SA?) phase on both heating and cooling cycles, while the tetrachloroaluminates exhibited chiral nematic (N?) phase. The mesophase was confirmed by characteristic LC textures observed by polarizing optical microscopy and typical diffractogram obtained by X-ray diffraction measurements. The samples with similar cholesteryl-linkage component showed similar phase transition temperature and entropy, indicating the cholesteryl component influence predominately on the phase transition rather than alkyl substituents on the imidazole ring. The imidazolium tetrachloroaluminates display relatively low phase transition temperature compared with the precursor chlorides. The functional difference in LC behavior and ionic conductivity were discussed by investigated the structural difference between the Cl--containing and AlCl4 - containing materials. The imidazolium chlorides exhibited layer structure both in crystal and mesophase states, and should be organized with a 'head-to-tail' organization to form interdigitated monolayer structures due to the tight ion pairs. But the imidazolium tetrachloroaluminates displayed layer structure only in crystal phase, and should be organized in 'head-to-head' arrangements form bilayer structures due to loose combination of ion pairs despite of hydrogen-bond and electrostatic attraction interaction.
A sulfonyl hydrazone cholesterol conjugate: Gelation, anion interaction and its application in dye adsorption
Panja, Atanu,Ghosh, Sumit,Ghosh, Kumaresh
, p. 10270 - 10277 (2019)
Cholesterol appended sulfonyl hydrazone derivative 1 was designed and synthesized as a supramolecular gelator for anionic sensing and dye adsorption. Gelator 1 forms a stable gel in DMSO-H2O. The intermolecular H-bonding involving the sulfonamide moieties and the hydrophobic interactions between the cholesterol units encourage gelation. The SEM images of the xerogels show tiny rod-like fibrous structures. The rheological studies of the gel reveal the viscoelastic nature of the material. The gels of 1 exhibit a sharp and selective response toward CN- and F- ions causing gel-to-sol transformation. The gels of 1 also show potential for application in adsorption and removal of anionic dyes, such as erythrosine B and uranine, from water. Preparation of a gel column was done with the gel of 1 which shows reasonably high one-time erythrosine B removal efficiency establishing its potential and promising real-life applicability in water purification.
Circularly polarized luminescence based on cholesterol-tetraphenylethylene-perylene liquid crystal
Chen, Ying,Guo, Hongyu,Jiang, Shengjie,Yang, Fafu,Zhou, Shujuan
supporting information, (2021/11/17)
Perylene derivative with circularly polarized luminescence (CPL) at aggregated state was seldom reported due to the strong ACQ (aggregation-caused quench) effect at aggregation. In this work, a novel cholesterol-tetraphenylethylene-perylene derivative (TPE-P) was designed and synthesized in moderate yield. It exhibited liquid crystalline behavior with orderly hexagonal columnar mesophase and good fluorescence emission at long wavelength (600-700 nm) not only in solution but also at aggregated states based on the AIE (aggregation-induced emission)-FRET (fluorescence resonance energy transfer) effect between tetraphenylethylene unit and perylene moiety. Moreover, the circular dichroism (CD) and CPL studies suggested the effective chiral transfer from cholesterol unit to tetraphenylethylene unit and perylene skeleton due to the spiral liquid crystalline self-assembly. The CD and CPL signals showed the order of THF lum| value for mesophase excited at 320 nm was as high as 1.5×10?2 based on the combining effect of AIE-FRET and chiral transfer. This research not only reported a novel CPL perylene derivative at aggregated state, but also confirmed that the combination of AIE-FRET effect and chiral transfer of liquid crytalline phase was an effective method to construct normal dye with excellent CPL property in aggregated state.
