Emeritus Professor Carl Redshaw's Outputs (26)

Synthesis of mono-O-alkylated homooxacalix[3]arene and a protection–deprotection strategy for homooxacalix[3]arene (2016)
Journal Article
Wu, C., Ikejiri, Y., Zeng, X., Elsegood, M. R., Redshaw, C., & Yamato, T. (2017). Synthesis of mono-O-alkylated homooxacalix[3]arene and a protection–deprotection strategy for homooxacalix[3]arene. Organic Letters, 19(1), 66-69. https://doi.org/10.1021/acs.orglett.6b03338

The regioselective synthesis of mono-O-alkylated homooxacalix[3]arene is accomplished for the first time. The synthetic route relies on two key steps: (i) a facile protection of two OH groups at the lower rim of the homooxacalix[3]arene and (ii) th... Read More about Synthesis of mono-O-alkylated homooxacalix[3]arene and a protection–deprotection strategy for homooxacalix[3]arene.

D-π-D chromophores based on dithieno[3,2-b:2′,3'-d]thiophene (DTT) : potential application in the fabrication of solar cell (2016)
Journal Article
Akther, T., Feng, X., Elsegood, M. R., Elsegood, M. R., Wang, C.-Z., Do, J.-H., Akther, T., Xing, F., Horsburgh, L., Elsegood, M., Redshaw, C., & Yamato, T. (2017). D-π-D chromophores based on dithieno[3,2-b:2′,3'-d]thiophene (DTT) : potential application in the fabrication of solar cell. Tetrahedron, 73(4), 307-312. https://doi.org/10.1016/j.tet.2016.11.077

In this work, four stable dithieno[3,2-b:2′,3'-d]thiophene-based π-extended molecules were designed and synthesized via a Pd-catalysed Sonogashira coupling reaction. The structures of these symmetrical compounds, including dithieno[3,2-b:2′,3'-d]thio... Read More about D-π-D chromophores based on dithieno[3,2-b:2′,3'-d]thiophene (DTT) : potential application in the fabrication of solar cell.

Reduction of diphenylacetylene using Al powder in the presence of noble metal catalysts in water (2016)
Journal Article
Rayhan, U., Kowser, Z., Redshaw, C., & Yamato, T. (2016). Reduction of diphenylacetylene using Al powder in the presence of noble metal catalysts in water. Tetrahedron, 72(44), 6943-6947. https://doi.org/10.1016/j.tet.2016.09.021

Diphenylacetylenes can be reduced to the corresponding diphenylethanes (2) in water in excellent yield using Al powder and Pd/C at 60 °C for 3 h in a sealed tube. In addition, the complete reduction of both aromatic rings required 80 °C for 15 h with... Read More about Reduction of diphenylacetylene using Al powder in the presence of noble metal catalysts in water.

A study of anion binding behaviour of 1,3-alternate thiacalix[4]arene-based receptors bearing urea moieties (2016)
Journal Article
Rahman, S., Tomiyasu, H., Kawazoe, H., Zhao, J.-L., Cong, H., Ni, X.-L., Zeng, X., Elsegood, M. R. J., Warwick, T. G., Teat, S. J., Redshaw, C., Georghiou, P. E., & Yamato, T. (2016). A study of anion binding behaviour of 1,3-alternate thiacalix[4]arene-based receptors bearing urea moieties. New journal of chemistry = Nouveau journal de chimie, 40(11), 9245-9251. https://doi.org/10.1039/c6nj00923a

© 2016 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique. Three novel thiacalix[4]arene receptors 4 a-c each with a 1,3-alternate conformation and possessing two urea moieties linking various phenyl groups substitute... Read More about A study of anion binding behaviour of 1,3-alternate thiacalix[4]arene-based receptors bearing urea moieties.

An unprecedented photochemical reaction for anthracene-containing derivatives (2016)
Journal Article
Zhao, J.-L., Jiang, X.-K., Wu, C., Wang, C.-Z., Zeng, X., Redshaw, C., & Yamato, T. (2016). An unprecedented photochemical reaction for anthracene-containing derivatives. Chemphyschem, 17(20), 3217-3222. https://doi.org/10.1002/cphc.201600783

A series of anthracene-containing derivatives have been synthesised and characterised. The photochemical behaviour of these derivatives have been investigated by 1 H NMR spectroscopy. An unprecedented photolysis reaction for anthracene-containing de... Read More about An unprecedented photochemical reaction for anthracene-containing derivatives.

A novel fluorescence “on–off–on” chemosensor for Hg²⁺ via a water-assistant blocking heavy atom effect (2016)
Journal Article
Wu, C., Zhao, J.-L., Jiang, X.-K., Wang, C.-Z., Ni, X.-L., Zeng, X., Redshaw, C., & Yamato, T. (2016). A novel fluorescence “on–off–on” chemosensor for Hg²⁺ via a water-assistant blocking heavy atom effect. Dalton Transactions : an international journal of inorganic chemistry, 45(38), 14948-14953. https://doi.org/10.1039/c6dt02274j

Upper rim pyrene-functionalized hexahomotrioxacalix[3]arene L was synthesized via Click chemistry, and its fluorescence behaviors toward several common metal cations were investigated. L exhibited a significant fluorescence quenching response to Hg²⁺... Read More about A novel fluorescence “on–off–on” chemosensor for Hg²⁺ via a water-assistant blocking heavy atom effect.

Synthesis, structures and conformational studies of 1,2-dimethyl[2.10]metacyclophane-1-enes (2016)
Journal Article
Akther, T., Islam, M. M., Rahman, S., Georghiou, P. E., Matsumoto, T., Tanaka, J., Thuéry, P., Redshaw, C., & Yamato, T. (2016). Synthesis, structures and conformational studies of 1,2-dimethyl[2.10]metacyclophane-1-enes. ChemistrySelect, 1(13), 3594-3600. https://doi.org/10.1002/slct.201600670

A series of 1,2-dimethyl[2.10]metacyclophan-1-enes (MCP-1-enes) containing different substituent groups has been synthesized to illustrate their conformational behavior. 4,22-dimethoxy-1,2-dimethyl[2.10]MCP-1-ene 3 was synthesized by a Grignard coupl... Read More about Synthesis, structures and conformational studies of 1,2-dimethyl[2.10]metacyclophane-1-enes.

Supramolecular assemblies constructed from inverted cucurbit[7]uril and lanthanide cations: synthesis, structure and sorption properties (2016)
Journal Article
Li, Q., Qiu, S.-C., Zhang, Y.-Q., Xue, S.-F., Tao, Z., Prior, T. J., Redshaw, C., Zhu, Q.-J., & Xiao, X. (in press). Supramolecular assemblies constructed from inverted cucurbit[7]uril and lanthanide cations: synthesis, structure and sorption properties. RSC advances, 6(81), 77805-77810. https://doi.org/10.1039/c6ra15559f

The interaction of a series of lanthanide cations (Ln³⁺) with inverted cucurbit[7]uril (iQ[7]) in the presence of [ZnCl₄]²⁻ anions as a structure-directing agent have been investigated. Single-crystal X-ray diffraction analysis has revealed that the... Read More about Supramolecular assemblies constructed from inverted cucurbit[7]uril and lanthanide cations: synthesis, structure and sorption properties.

“Janus” calixarenes: double–sided molecular linkers for facile, multi-anchor point, multi-functional, surface modification (2016)
Journal Article
Buttress, J. P., Day, D. P., Courtney, J. M., Lawrence, E. J., Hughes, D. L., Blagg, R. J., Crossley, A., Matthews, S. E., Redshaw, C., Page, P. C. B., & Wildgoose, G. G. (2016). “Janus” calixarenes: double–sided molecular linkers for facile, multi-anchor point, multi-functional, surface modification. Langmuir : the ACS journal of surfaces and colloids, 32(31), 7806-7813. https://doi.org/10.1021/acs.langmuir.6b02222

We herein report the synthesis of novel "Janus" calix[4]arenes bearing four "molecular tethering" functional groups on either the upper or lower rims of the calixarene. These enable facile multipoint covalent attachment to electrode surfaces with mon... Read More about “Janus” calixarenes: double–sided molecular linkers for facile, multi-anchor point, multi-functional, surface modification.

Click-modified hexahomotrioxacalix[3]arenes as fluorometric and colorimetric dual-modal chemosensors for 2,4,6-trinitrophenol (2016)
Journal Article
Wu, C., Zhao, J. L., Jiang, X. K., Ni, X. L., Zeng, X., Redshaw, C., & Yamato, T. (2016). Click-modified hexahomotrioxacalix[3]arenes as fluorometric and colorimetric dual-modal chemosensors for 2,4,6-trinitrophenol. Analytica Chimica Acta, 936, 216-221. https://doi.org/10.1016/j.aca.2016.06.045

A new type of chemosensor-based approach to the detection of 2,4,6-trinitrophenol (TNP) is described in this paper. Two hexahomotrioxacalix[3]arene-based chemosensors 1 and 2 were synthesized through click chemistry, which exhibited high binding affi... Read More about Click-modified hexahomotrioxacalix[3]arenes as fluorometric and colorimetric dual-modal chemosensors for 2,4,6-trinitrophenol.

Synthesis and evaluation of a novel fluorescent sensor based on hexahomotrioxacalix[3]arene for Zn²+ and Cd²+ (2016)
Journal Article
Jiang, X.-K., Ikejiri, Y., Jin, C.-C., Wu, C., Zhao, J.-L., Ni, X.-L., Zeng, X., Redshaw, C., & Yamato, T. (2016). Synthesis and evaluation of a novel fluorescent sensor based on hexahomotrioxacalix[3]arene for Zn²+ and Cd²+. Tetrahedron, 72(32), 4854-4858. https://doi.org/10.1016/j.tet.2016.06.055

A novel type of selective and sensitive fluorescent sensor having triazole rings as the binding sites on the lower rim of a hexahomotrioxacalix[3]arene scaffold in a cone conformation is reported. This sensor has desirable properties for practical ap... Read More about Synthesis and evaluation of a novel fluorescent sensor based on hexahomotrioxacalix[3]arene for Zn²+ and Cd²+.

Structural studies of Schiff-base [2 + 2] macrocycles derived from 2,2′-oxydianiline and the ROP capability of their organoaluminium complexes (2016)
Journal Article
Yang, W., Zhao, K.-Q., Prior, T. J., Hughes, D. L., Arbaoui, A., Elsegood, M. R. J., & Redshaw, C. (2016). Structural studies of Schiff-base [2 + 2] macrocycles derived from 2,2′-oxydianiline and the ROP capability of their organoaluminium complexes. Dalton Transactions : an international journal of inorganic chemistry, 45(30), 11990-12005. https://doi.org/10.1039/c6dt01997h

The molecular structures of a number of solvates of the [2+2] Schiff-base macrocycles {[2-(OH)-5-(R)-C₆H₂-1,3-(CH)₂][O(2-C₆H₄N)₂]}₂ (R = Me L¹H₂, tBu L²H₂, Cl L³H₂), formed by reacting 2,6-dicarboxy-4-R-phenol with 2,2/-oxydianiline (2-aminophenyleth... Read More about Structural studies of Schiff-base [2 + 2] macrocycles derived from 2,2′-oxydianiline and the ROP capability of their organoaluminium complexes.

Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties (2016)
Journal Article
Feng, X., Seto, N., Wang, C.-Z., Matsumoto, T., Tanaka, J., Wei, X.-F., Elsegood, M. R., Horsburgh, L., Redshaw, C., & Yamato, T. (2016). Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties. ChemistrySelect, 1(9), 1926-1932. https://doi.org/10.1002/slct.201600598

This article presents a set of extended π-conjugated pyrene derivatives, namely 1,3-di(arylethynyl)-7-tert-butylpyrenes, which were synthesized by a Pd-catalyzed Sonogashira coupling reaction of 1,3-dibromo-7-tert-butylpyrenes with the corresponding... Read More about Extended π-conjugated pyrene derivatives: structural, photophysical and electrochemical properties.

A ratiometric Al³⁺ ion probe based on the coumarin-quinoline FRET system (2016)
Journal Article
Zhu, Q., Li, L., Mu, L., Zeng, X., Redshaw, C., & Wei, G. (2016). A ratiometric Al³⁺ ion probe based on the coumarin-quinoline FRET system. Journal of Photochemistry and Photobiology A: Chemistry, 328, 217-224. https://doi.org/10.1016/j.jphotochem.2016.06.006

A coumarin-quinoline based fluorescence resonance energy transfer (FRET) system (TCQ) has been synthesized and employed as a ratiometric fluorescence probe. The selective fluorescent response of the probe TCQ toward Al³⁺ was devised by employing a qu... Read More about A ratiometric Al³⁺ ion probe based on the coumarin-quinoline FRET system.

Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies (2016)
Journal Article
Kowser, Z., Jin, C.-C., Jiang, X., Rahman, S., Georghiou, P. E., Ni, X.-L., Zeng, X., Redshaw, C., & Yamato, T. (2016). Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies. Tetrahedron, 72(30), 4575-4581. https://doi.org/10.1016/j.tet.2016.06.017

A new fluorescent chemosensor L1, pyrene containing long chain Schiff base derivative in 1-position has been synthesized. Similarly, the receptors L2 and L3 are also designed in order to compare the binding ability for detection of Cu2+. The receptor... Read More about Fluorescent turn-on sensors based on pyrene-containing Schiff base derivatives for Cu2+ recognition: spectroscopic and DFT computational studies.

Thiacalix[4]arene derivatives bearing imidazole units : a ditopic hard/soft receptor for Na⁺ and K⁺/Ag⁺ with an allosteric effect and a reusable extractant for dichromate anions (2016)
Journal Article
Zhao, J.-L., Wu, C., Zeng, X., Rahman, S., Georghiou, P. E., Elsegood, M. R., Warwick, T. G., Redshaw, C., Teat, S. J., & Yamato, T. (2016). Thiacalix[4]arene derivatives bearing imidazole units : a ditopic hard/soft receptor for Na⁺ and K⁺/Ag⁺ with an allosteric effect and a reusable extractant for dichromate anions. ChemistrySelect, 1(8), 1541-1547. https://doi.org/10.1002/slct.201600245

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Two novel receptors 5,11,17,23-tetra-tert-butyl-25,27-bis[(ethoxycarbonyl)methoxy]-26,28-bis-[1-methyl-(imidazole)meth-oxy] -2,8,14,20-tetra-thiacalix[4]arene (L1) and 5,11,17,23-tetra-tert-butyl-25... Read More about Thiacalix[4]arene derivatives bearing imidazole units : a ditopic hard/soft receptor for Na⁺ and K⁺/Ag⁺ with an allosteric effect and a reusable extractant for dichromate anions.

Interaction of a symmetrical α,α',δ,δ'-Tetramethyl-cucurbit[6]uril with Ln³⁺ : potential applications for isolation of lanthanides (2016)
Journal Article
Yang, B., Gao, Z.-Z., Lu, J.-H., Zhu, Q.-J., Xue, S.-F., Tao, Z., Prior, T. J., Redshaw, C., Wei, G., & Xiao, X. (2016). Interaction of a symmetrical α,α',δ,δ'-Tetramethyl-cucurbit[6]uril with Ln³⁺ : potential applications for isolation of lanthanides. CrystEngComm RSC, 18(26), 5028-5035. https://doi.org/10.1039/c6ce00134c

The interaction of a symmetrical α,α′,δ,δ′-tetramethyl-cucurbit[6]uril (TMeQ[6]) with a series of lanthanide cations (Ln³⁺) was investigated in neutral water and in acidic solution. Analysis by single crystal X-ray diffraction revealed that different... Read More about Interaction of a symmetrical α,α',δ,δ'-Tetramethyl-cucurbit[6]uril with Ln³⁺ : potential applications for isolation of lanthanides.

Demethylation of 5,n-di-tert-butyl-8,n-dimethoxy[2.n] metacyclophane-1-ynes with BBr3 to afford novel [n] benzofuranophanes (2016)
Journal Article
Akther, T., Islam, M. M., Matsumoto, T., Tanaka, J., Feng, X., Redshaw, C., & Yamato, T. (2016). Demethylation of 5,n-di-tert-butyl-8,n-dimethoxy[2.n] metacyclophane-1-ynes with BBr3 to afford novel [n] benzofuranophanes. Journal of molecular structure, 1122(15 October), 247-255. https://doi.org/10.1016/j.molstruc.2016.05.054

© 2016 Elsevier B.V. All rights reserved. Novel [n]benzofuranophanes (n = 8 & 10) 2a-b have been prepared by successive intramolecular cyclization from 5,19-di-tert-butyl-8,22-dimethoxy[n]metacyclophane-1-yne (syn-1a-b) by treatment with BBr 3 in C... Read More about Demethylation of 5,n-di-tert-butyl-8,n-dimethoxy[2.n] metacyclophane-1-ynes with BBr3 to afford novel [n] benzofuranophanes.

Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans (2016)
Journal Article
Islam, M. M., Akther, T., Ikejiri, Y., Matsumoto, T., Tanaka, J., Rahman, S., Georghiou, P. E., Hughes, D. L., Redshaw, C., & Yamato, T. (in press). Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans. RSC advances, 6(56), 50808-50817. https://doi.org/10.1039/c6ra06219a

Calix[3]benzofurans have been synthesized by a modified TosMIC coupling reaction, followed by acid treatment and an intramolecular cyclization reaction with TMSI (trimethylsilyl iodide); X-ray analysis established the structures of two samples, both... Read More about Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3]benzofurans.

Metallocalixarene catalysts: α-olefin polymerization and ROP of cyclic esters (2016)
Journal Article
Redshaw, C. (2016). Metallocalixarene catalysts: α-olefin polymerization and ROP of cyclic esters. Dalton Transactions : an international journal of inorganic chemistry, 45(22), 9018-9030. https://doi.org/10.1039/c6dt01529h

This perspective review discusses metallocalix[n]arene complexes that have been employed in either α-olefin polymerization or in the ring opening polymerization (ROP) of cyclic esters over the last 5 years. Synthesis, molecular structure and catalyti... Read More about Metallocalixarene catalysts: α-olefin polymerization and ROP of cyclic esters.