Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes: Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes (2017)
Journal Article
Thuéry, P., Islam, M. M., Akther, T., Islam, M. M., Matsumoto, T., Tanaka, J., …Yamato, T. (2017). Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes: Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes. European Journal of Organic Chemistry, 2017(13), 1721-1726. https://doi.org/10.1002/ejoc.201601647

Bromination of 5,21-di-tert-butyl-8,24-dimethoxy-1,2-dimethyl[2.10]metacyclophan-1-ene (MCP-1-ene; 1) with benzyltrimethylammonium tribromide exclusively afforded 1,2-bis(bromomethyl)-5,21-di-tert-butyl-8,24-dimethoxy[2.10]MCP-1-ene (2). Debrominatio... Read More about Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes: Synthesis and Structure of 1,2-Dimethylene[2.10]metacyclophane and Its Conversion into Chiral [10]Benzenometacyclophanes.

Organoaluminium complexes derived from Anilines or Schiff bases for ring opening polymerization of epsilon-caprolactone, delta-valerolactone and rac-lactide (2017)
Journal Article
Mo, S., Prior, T. J., Al-Khafaj, Y., Zhao, K., Wang, X., Elsegood, M. R., …Redshaw, C. (2017). Organoaluminium complexes derived from Anilines or Schiff bases for ring opening polymerization of epsilon-caprolactone, delta-valerolactone and rac-lactide. European Journal of Inorganic Chemistry, 2017(13), 1951-1965. https://doi.org/10.1002/ejic.201601415

Reaction of R¹R²CHN=CH(3,5-tBu₂C₆H₂-OH-2) (R¹ = R² = Me L¹H; R¹ = Me, R² = Ph L²H; R¹ = R2 = Ph L³H) with one equivalent of R³3Al (R³ = Me, Et) afforded [(L¹-³)AlR³₂] (L¹, R³ = Me 1, R³ = Et 2; L², R³ = Me 3, R³ = Et 4; L³ R³ = Me 5, R³ = Et 6); comp... Read More about Organoaluminium complexes derived from Anilines or Schiff bases for ring opening polymerization of epsilon-caprolactone, delta-valerolactone and rac-lactide.

Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes (2017)
Journal Article
Akther, T., Islam, M. M., Rahman, S., Georghiou, P. E., Matsumoto, T., Tanaka, J., …Yamato, T. (2017). Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes. Organic & biomolecular chemistry, 15(16), 3519-3527. https://doi.org/10.1039/C7OB00400A

A series of syn- and anti-[2.n]metacyclophan-1-enes have been prepared in good yields by McMurry cyclizations of 1,n-bis(5-tert-butyl-3-formyl-2-methoxyphenyl)alkanes. Significantly, acid catalyzed rearrangements of [2.n]metacyclophan-1-enes afforded... Read More about Synthesis and conformations of [2.n]metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes.

Supramolecular assembly of cucurbit[6]uril and N-butyl-4-pyrrolidinopyridine (2017)
Journal Article
Hou, H., Gao, Z., Bai, D., Tao, Z., Prior, T. J., Redshaw, C., & Xiao, X. (2017). Supramolecular assembly of cucurbit[6]uril and N-butyl-4-pyrrolidinopyridine. Supramolecular chemistry, 29(9), 680-685. https://doi.org/10.1080/10610278.2017.1304549

The nature of the supramolecular host-guest complex involving 4-pyrrolidinopyridine (BuPC4) and cucurbit[6]uril (Q[6]) has been investigated by NMR and UV spectroscopy, MALDI-TOF mass spectrometry, X-ray crystallography and isothermal titration calor... Read More about Supramolecular assembly of cucurbit[6]uril and N-butyl-4-pyrrolidinopyridine.

Alkyl substituted cucurbit[6]uril assisted competitive fluorescence recognition of lysine and methionine in aqueous solution (2017)
Journal Article
Bai, Q., Zhang, S., Chen, H., Sun, T., Redshaw, C., Zhang, J., …Tao, Z. (2017). Alkyl substituted cucurbit[6]uril assisted competitive fluorescence recognition of lysine and methionine in aqueous solution. ChemistrySelect, 2(8), 2569-2573. https://doi.org/10.1002/slct.201700053

The use of competitive ratiometric fluorescence indicator displacement chemosensors derived from two alkyl substituted cucurbit[6]uril-based host-guest complexes is reported. In particular, the differing binding abilities of two cucurbit[6]uril deriv... Read More about Alkyl substituted cucurbit[6]uril assisted competitive fluorescence recognition of lysine and methionine in aqueous solution.

Synthesis, structure and photophysical properties of pyrene–based [5]helicenes : an experimental and theoretical study (2017)
Journal Article
Thuéry, P., Wang, C., Kihara, R., Feng, X., Thuery, P., Redshaw, C., & Yamato, T. (2017). Synthesis, structure and photophysical properties of pyrene–based [5]helicenes : an experimental and theoretical study. ChemistrySelect, 2(4), 1436-1441. https://doi.org/10.1002/slct.201601327

Pyrene-cored [5]helicenes were prepared by a facile, efficient Wittig reaction and an intramolecular photocyclization reaction utilising 2,7-di-tert-butylpyrene-4-carbaldehyde and naphthalene/pyrene-based phosphorus ylides. Optical properties based o... Read More about Synthesis, structure and photophysical properties of pyrene–based [5]helicenes : an experimental and theoretical study.

Multimetallic lithium complexes derived from the acids Ph₂C(X)CO₂H (X = OH, NH₂) : synthesis, structure and ring opening polymerization of lactides and lactones (2017)
Journal Article
Al-Khafaji, Y. F., Prior, T. J., Horsburgh, L., Elsegood, M. R. J., & Redshaw, C. (2017). Multimetallic lithium complexes derived from the acids Ph₂C(X)CO₂H (X = OH, NH₂) : synthesis, structure and ring opening polymerization of lactides and lactones. ChemistrySelect, 2(2), 759-768. https://doi.org/10.1002/slct.201602029

Reaction of LiOR (R=t-Bu, Ph) with the acids 2,2/-Ph₂C(X)(CO₂H), X=OH (benzH), NH₂ (dpgH) was investigated. For benzH, one equivalent LiOt-Bu in THF afforded [Li(benz)]2⋅2THF (1⋅2THF), which adopts a 1D chain structure. If acetonitrile is used (mild... Read More about Multimetallic lithium complexes derived from the acids Ph₂C(X)CO₂H (X = OH, NH₂) : synthesis, structure and ring opening polymerization of lactides and lactones.

A study of the interaction between inverted cucurbit[7]uril and symmetric viologens (2017)
Journal Article
Gao, Z., Chen, L., Gao, Z., Bai, D., Chen, L., Tao, Z., …Redshaw, C. (2017). A study of the interaction between inverted cucurbit[7]uril and symmetric viologens. RSC advances, 7(1), 461-467. https://doi.org/10.1039/c6ra24780f

The interaction between inverted cucuribit[7]uril (iQ[7]) and a series of symmetric viologen derivatives bearing aliphatic substituents of variable length, namely dicationic dialkyl-4,4′-bipyridinium guests where the alkyl is CH₃(CH₂)n with n = 0 to... Read More about A study of the interaction between inverted cucurbit[7]uril and symmetric viologens.

Chemosensor for micro to nano-molar detection of Ag+ and Hg2+ ions in pure aqueous media and its applications in cell imaging (2017)
Journal Article
Nandre, J. P., Patil, S. R., Sahoo, S. K., Pradeep, C. P., Churakov, A., Yu, F., …Patil, U. D. (2017). Chemosensor for micro to nano-molar detection of Ag+ and Hg2+ ions in pure aqueous media and its applications in cell imaging. Dalton Transactions : an international journal of inorganic chemistry, 46(41), 14201-14209. https://doi.org/10.1039/C7DT02524F

The pyridine substituted thiourea derivative PTB-1 was synthesized and characterized by spectroscopic techniques as well as by single crystal X-ray crystallography. The metal ion sensing ability of PTB-1 was explored by various experimental (naked-ey... Read More about Chemosensor for micro to nano-molar detection of Ag+ and Hg2+ ions in pure aqueous media and its applications in cell imaging.

Ring opening polymerization of lactides and lactones by multimetallic alkyl zinc complexes derived from the acids Ph₂C(X)CO₂2H (X = OH, NH₂ ) (2017)
Journal Article
Al-Khafaji, Y. F., Elsegood, M. R. J., Frese, J. W. A., Elsegood, M. R., Frese, J. W., Al-Khafaji, Y., …Frese, J. (2017). Ring opening polymerization of lactides and lactones by multimetallic alkyl zinc complexes derived from the acids Ph₂C(X)CO₂2H (X = OH, NH₂ ). RSC advances, 7(8), 4510-4517. https://doi.org/10.1039/C6RA26746G

The reaction of the dialkylzinc reagents R₂Zn with the acids 2,2-Ph₂C(X)(CO₂H), where X = NH₂, OH, i.e. 2,2′-diphenylglycine (dpgH) or benzilic acid (benzH2), in toluene at reflux temperature afforded the tetra-nuclear ring complexes [RZn(dpg)]₄, whe... Read More about Ring opening polymerization of lactides and lactones by multimetallic alkyl zinc complexes derived from the acids Ph₂C(X)CO₂2H (X = OH, NH₂ ).

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., Do, J., …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., Cong, H., Ni, X., …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., Jiang, X., Wu, C., Wang, C., 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., Jiang, X., Wang, C., Ni, X., Zeng, X., …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., …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., Zhang, Y., Xue, S., Tao, Z., Prior, T. 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., …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.