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Chomchai Suksai Pannee Leeladee Colin Jennings Thawatchai Tuntulani Palangpon Kongsaeree 《Journal of chemical crystallography》2008,38(5):363-368
Abstract The reaction of 1,1′-bis(chlorocarbonyl)ferrocene with bis-aminobenzylcalix[4]arene gave amidoferrocene calix[4]arene monomer
1. Compound 1 crystallized in the monoclinic system P21/c with a = 11.196(6) ?, b = 14.971(11) ?, c = 32.007(2) ?, β = 96.413(4)° and V = 5330.9(6) ?3. X-ray diffraction analyses of 1 showed that the calix[4]arene scaffold was in cone conformation in which the intramolecular hydrogen bonding were formed
through OH groups at the lower rim to stabilize the structure. Moreover, the intramolecular hydrogen bond between the amide
groups of the amidoferrocene unit also presented in the crystal structure. On the other hand, the condensation of 1,1′-bis(chlorocarbonyl)ferrocene
with p-tert-bis-aminobenzylcalix[4]arene resulted in the monomeric 2 and [2 + 2] dimeric compounds 3. 1H-NMR studies signified that the calix[4]arene building block in compounds 2 and 3 adopted the cone conformation.
Index Abstract Synthesis and Characterization of Monomeric and Dimeric Structures of Calix[4]arenes Containing Amidoferrocene
Chomchai Suksai*, Pannee Leeladee, Colin Jennings, Thawatchai Tuntulani*, Palangpon Kongsaeree
The condensation of 1,1′-bis(chlorocarbonyl)ferrocene with p-tert-bis-aminobenzylcalix[4]arene resulted in the monomeric and [2 + 2] dimeric compounds.
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Sarayut Watchasit Chomchai Suksai Thawatchai Tuntulani Chaveng Pakawatchai 《Tetrahedron letters》2010,51(26):3398-86
Mono- and dinuclear Cu(II) complexes of p-tert-butylcalix[4]arene (CuL1 and CuL2, respectively) were synthesized, and their anion recognition abilities were explored. Recognition is efficiently signaled through the displacement of pyrocatechol violet bound to the receptor. For CuL2, recognition selectivity is ascribed to the tuning of the distance between donor atoms of anion guests and their ability to encompass the Cu2+-Cu2+ distance within the cleft of CuL2. In addition, the preorganization of calix[4]arene in the cone conformation and steric hindrance of two bulky tripodal amine moieties are important factors in controlling the Cu2+-Cu2+ distance. These factors caused CuL2 to recognize pyrophosphate selectively with respect to other inorganic anions in 80/20 (v/v%) MeCN/H2O solution buffered with 10 mM HEPES at pH 6.4. 相似文献
3.
Chromogenic anion sensors 总被引:1,自引:0,他引:1
Chromogenic sensors for anions generally consist of two parts: anion receptors and chromophores. In this review, 6 types of chromogenic anion sensors are described, namely, NH-based hydrogen bonding, Lewis acid, metal-ion template, transition metal complexes, chromogenic guest displacement and chromoreactands. The first 4 types possess anion receptors attached directly to the chromophores while the guest displacement techniques employ indicators as the ones that were replaced by specific anions. The last type has emerged recently and uses specific reactions between chromogenic hosts or indicators and particular anions to cause dramatic colour changes. 相似文献
4.
Chomchai Suksai Disyaphong Jainuknan Nongnuch Muangsin Palangpol Kongsaeree 《Tetrahedron letters》2005,46(16):2765-2769
The heteroditopic receptor 2 containing a crown ether and amidoferrocence groups was synthesized and the binding abilities with various anions are reported in the presence and absence of metal cations. In the presence of Na+, 2 showed positive co-operative binding towards Br− with the binding affinity Kass = 16,096 M−1. Therefore, receptor 2 showed a switched-on binding for Br− in the presence of Na+ and a switched-off binding in the absence of Na+. Compound 2 was also found to sense Cl− and Br− electrochemically. 相似文献
5.
Chomchai Suksai Chaveng Pakawatchai Thawatchai Tuntulani 《Journal of chemical crystallography》2009,39(5):348-352
Abstract The crystal structures of pyridine containing thiourea moieties as substituents, (1) and (2), have been determined. The ortho-substituted pyridine (1) crystallized in monoclinic space group P21/c with a = 16.091(3) ?, b = 11.368(2) ?, c = 7.4364(14) ?, β = 100.489(4)o, V = 1337.5(4) ?3, z = 4. In this structure an intramolecular N–H···N hydrogen bond forms a pseudo-seven-membered ring. The meta-substituted pyridine (2) crystallized in monoclinic space group P21/c with a = 14.5408(15) ?, b = 8.8508(9) ?, c = 10.7959(11) ?, β = 106.435(2)o, V = 1332.6(2) ?3, z = 4. Crystal packing revealed that compounds (1) and (2) can form dimeric structures via intermolecular H-bonding using N–H···S and N–H···N interactions, respectively.
Graphical Abstract Varying the substituent position on the pyridine ring using thiourea moieties gave unique molecular aggregations in solid
state structures.
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6.
Suksai C Figueiras Gómez S Chhabra A Liu J Skepper JN Tuntulani T Otto S 《Langmuir : the ACS journal of surfaces and colloids》2006,22(14):5994-5997
A new amphiphilic receptor containing a macrocyclic anionic headgroup and a single alkyl chain was prepared through an efficient templated synthesis. The interdependence of the aggregation behavior and the host-guest chemistry was studied. In the absence of any guest the terminus of the alkyl chain of the receptor is included inside the hydrophobic cavity of the macrocycle (as evident from 1H NMR studies) leading to self-assembly into micrometer-long nanotubes (as evident from TEM studies). The alkyl chain can be displaced by an acridizinium bromide guest (as evident from 1H NMR and ITC), which leads to a dramatic change in aggregate size and morphology (as evident from DLS). Studies of the solubilization of Nile red suggest that the resulting aggregates are micelles with a cmc of around 35 microM. These results represent a new addition to the still small number of water-soluble amphiphilic receptors and one of the first examples in which specific host-guest chemistry controls the size and shape of nanoscale aggregates. 相似文献
7.
Nisachol NerngchamnongBenjamas Chailap Pannee LeeladeeOrawon Chailapakul Chomchai Suksai Thawatchai Tuntulani 《Tetrahedron letters》2011,52(22):2914-2917
Two derivatives of p-tert-butylcalix[4]arenes 1 and 2 containing diethyl ester and amidoferrocene units as cation and anion binding sites, respectively, have been synthesized. Both compounds were isomeric with different topology for accommodating ions. 1H NMR spectroscopy, cyclic voltammetry, and square-wave voltammetry were used to study the binding abilities of receptors 1 and 2 toward anions. Both receptors were found to bind Br− and I− selectively in the presence of Na+. The electrochemically oxidized ferrocenium form of para-isomer 2 in the free form was found to sense AcO− selectively, but demonstrated a negative sensing in the presence of Na+. In contrast, the electrochemically oxidized ferrocenium form of meta-isomer 1 was found to enhance sensing of AcO− and Cl− in the presence of Na+. 相似文献
8.
New polymeric membrane cadmium(II)-selective electrodes using tripodal amine based ionophores 总被引:1,自引:0,他引:1
Khamjumphol U Watchasit S Suksai C Janrungroatsakul W Boonchiangma S Tuntulani T Ngeontae W 《Analytica chimica acta》2011,704(1-2):73-86
Fabrication of PVC membrane electrodes incorporating selective neutral carriers for Cd(2+) was reported. The ionophores were designed to have different topologies, donor atoms and lipophilicity by attaching tripodal amine (TPA) units to the lipophilic anthracene (ionophore I) and p-tert-butylcalix[4]arene (ionophores II, III and IV). The synthesized ionophores were incorporated to the plasticized PVC membranes to prepare Cd(II) ion selective electrodes (ISEs). The membrane electrodes were optimized by changing types and amounts of ionic sites and plasticizers. The selectivity of the membranes fabricated from the synthesized ionophores was evaluated, the relationship between structures of ionophores and membrane characteristics were explored. The ionophore IV which composed of two opposites TPA units on the calix[4]arene compartment showed the best selectivity toward Cd(2+). The best membrane electrode was fabricated from ionophore IV (10.2 mmol kg(-1)) with KTpClPB (50.1 mol% related to the ionophore) as an ion exchanger incorporated in the DOS plasticized PVC membrane (1:2; PVC:DOS). The Cd-ISE fabricated from ionophore IV exhibited good properties with a Nernstian response of 29.4±0.6 mV decade(-1) of activity for Cd(2+) ions and a working concentration range of 1.6×10(-6)-1.0×10(-2)M. The sensor has a fast response time of 10s and can be used for at least 1 week without any divergence in potential. The electrode can be used in the pH range of 6.0-9.0. The proposed electrodes using ionophores III and IV were employed as a probe for determining Cd(2+) from the oxidation of CdS QDs solution and the real treatment waste water sample with excellent results. 相似文献
9.
The synthesis and characterization of the amine–oxime complex [Ni(meso-HMPAO)–H] · ClO4 (1) and its oxidized Schiff-base product [Ni(meso-HMPAO)-5H] · ClO4 (2), where HMPAO is hexamethyl propylene amine oxime, are presented. Complex 2 results from the oxidation of 1 by molecular oxygen in basic aqueous solution. The structural change of the amine complex 1 to the Schiff-base complex 2 was investigated by the means of NMR spectroscopy and X-ray crystallography. 相似文献
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