Multimetallic lithium complexes derived from the acids Ph₂C(X)CO₂H (X = OH, NH₂) : synthesis, structure and ring opening polymerization of lactides and lactones

Al-Khafaji, Yahya F.; Prior, Timothy J.; Horsburgh, Lynne; Elsegood, Mark R. J.; Redshaw, Carl

doi:10.1002/slct.201602029

Reduction of phenylacetylenes using Raney Ni-Al alloy, Al powder in the presence of noble metal catalysts in water (2017)
Journal Article
Rayhan, U., Kowser, Z., Islam, M. N., Redshaw, C., & Yamato, T. (2017). Reduction of phenylacetylenes using Raney Ni-Al alloy, Al powder in the presence of noble metal catalysts in water. Arkivoc, 2018(2), 241-251. https://doi.org/10.24820/ark.5550190.p010.277

Dedicated to Prof. Kenneth Laali on the occasion of his 66th birthday Received mm-dd-yyyy Accepted mm-dd-yyyy Published on line mm-dd-yyyy Dates to be inserted by editorial office Abstract The chemoselective reduction is based on the reaction of Rane... Read More about Reduction of phenylacetylenes using Raney Ni-Al alloy, Al powder in the presence of noble metal catalysts in water.

Synthesis and structure of a chiral areno-bridged [2.4]metacyclophane (2017)
Journal Article
Islam, M., Akther, T., Matsumoto, T., Tanaka, J., Thuéry, P., Redshaw, C., & Yamato, T. (2018). Synthesis and structure of a chiral areno-bridged [2.4]metacyclophane. Tetrahedron, 74(2), 329-335. https://doi.org/10.1016/j.tet.2017.11.075

© 2017 Elsevier Ltd The reductive coupling reaction of 1,4-bis(3-acetyl-5-tert-butyl-2-methoxyphenyl)butane 3 was carried out using TiCl 4 -Zn in pyridine followed by a McMurry coupling reaction to afford the compounds anti and syn 1,2-dimethyl[2.4]M... Read More about Synthesis and structure of a chiral areno-bridged [2.4]metacyclophane.

Molybdocalix[4]arene N,O-Schiff-base ligands (2017)
Journal Article
Wang, X., Zhao, K. Q., Elsegood, M. R., & Redshaw, C. (2018). Molybdocalix[4]arene N,O-Schiff-base ligands. Supramolecular chemistry, 30(5-6), 404-410. https://doi.org/10.1080/10610278.2017.1403608

The ‘one-pot’ reaction of 2-hydroxy-3,5-di-tert-butylsalicylaldehyde with in situ generated ‘amino calixarene’ (from {Mo[(2-NC 6 H 4 ) 2 CH 2 CH 2 ]Cl 2 (DME)}, KOtBu and p-tert-butylcalix[4]areneH 4 LH 4 ) afforded, after work-up, the heterobimetall... Read More about Molybdocalix[4]arene N,O-Schiff-base ligands.

Highly selective recognition of Al3+ and I- ions using a bifunctional fluorescent probe (2017)
Journal Article
Li, Z., Zhao, J.-L., Wu, Y.-T., Mu, L., Zeng, X., Jin, Z., Wei, G., Xie, N., & Redshaw, C. (2017). Highly selective recognition of Al3+ and I- ions using a bifunctional fluorescent probe. Organic & biomolecular chemistry, 15(40), 8627-8633. https://doi.org/10.1039/C7OB02301D

A tripodal fluorescent probe L1 armed with rhodamine B and 1-naphthaleneisothiocyanates was prepared in high yield. A study of the recognition properties revealed that probe L1 exhibited high sensitivity and selectivity towards Al3⁺ through a “FRET”... Read More about Highly selective recognition of Al3+ and I- ions using a bifunctional fluorescent probe.

Synthesis, Conformational Properties and DFT Computational Studies of Polymethyl-Substituted [3.3]Metacyclophanes (2017)
Journal Article
Islam, M. M., Akther, T., Rahman, S., Georghiou, P. E., Matsumoto, T., Tanaka, J., Redshaw, C., & Yamato, T. (2017). Synthesis, Conformational Properties and DFT Computational Studies of Polymethyl-Substituted [3.3]Metacyclophanes. ChemistrySelect, 2(24), 7255-7262. https://doi.org/10.1002/slct.201701243

Polymethyl substituted [3.3]metacyclophanes (MCPs) 4 a–d, were synthesized by the TosMIC coupling method followed by Wolff–Kishner reduction of the corresponding polymethyl-substituted [3.3]MCP-2,11-diones (3 a–d). 1H NMR spectroscopy reveals that bo... Read More about Synthesis, Conformational Properties and DFT Computational Studies of Polymethyl-Substituted [3.3]Metacyclophanes.

Click synthesis of a quinoline-functionalized hexahomotrioxacalix[3]arene : a turn-on fluorescence chemosensor for Fe³⁺ (2017)
Journal Article
Wu, C., Wang, C.-Z., Zhu, Q., Zeng, X., Redshaw, C., & Yamato, T. (2018). Click synthesis of a quinoline-functionalized hexahomotrioxacalix[3]arene : a turn-on fluorescence chemosensor for Fe³⁺. Sensors and actuators. B, Chemical, 254, 52-58. https://doi.org/10.1016/j.snb.2017.07.048

A novel quinoline-functionalized hexahomotrioxacalix[3]arene L was synthesized via Click chemistry and its chemosensing properties with various metal ions were investigated. The chemosensor L exhibited a high selectivity for Fe³⁺ with little interfer... Read More about Click synthesis of a quinoline-functionalized hexahomotrioxacalix[3]arene : a turn-on fluorescence chemosensor for Fe³⁺.

Synthesis and structure of the inclusion complex {NdQ[5]K@Q[10](H₂O)4}·4NO₃·20H₂O (2017)
Journal Article
Chen, L. X., Kan, J. L., Cong, H., Prior, T. J., Tao, Z., Xiao, X., & Redshaw, C. (2017). Synthesis and structure of the inclusion complex {NdQ[5]K@Q[10](H₂O)4}·4NO₃·20H₂O. Molecules, 22(7), 1147. https://doi.org/10.3390/molecules22071147

Heating a mixture of Nd(NO₃)₃·6H₂O, KCl, Q[10] and Q[5] in HCl for 10 min affords the inclusion complex {NdQ[5]K@Q[10](H₂O)₄}·4NO₃·20H₂O. The structure of the inclusion complex has been investigated by single crystal X-ray diffraction and by X-ray Ph... Read More about Synthesis and structure of the inclusion complex {NdQ[5]K@Q[10](H₂O)4}·4NO₃·20H₂O.

A quinoline-based fluorometric and colorimetric dual-modal pH probe and its application in bioimaging (2017)
Journal Article
Zhu, Q., Li, Z., Mu, L., Zeng, X., Redshaw, C., & Wei, G. (2018). A quinoline-based fluorometric and colorimetric dual-modal pH probe and its application in bioimaging. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 188, 230-236. https://doi.org/10.1016/j.saa.2017.06.071

The compound (E)-8-hydroxyl-2-[(E)-2-(2, 4-dihydroxyphenyl)vinyl]-quinoline (1) has been developed as a fluorometric and colorimetric dual-modal probe for pH detection in solution and in vivo. Remarkable changes in the fluorescence intensity with lar... Read More about A quinoline-based fluorometric and colorimetric dual-modal pH probe and its application in bioimaging.

A pyrene-based approach to tune emission color from blue to yellow (2017)
Journal Article
Wang, C.-Z., Ichiyanagi, H., Sakaguchi, K., Feng, X., Elsegood, M. R., Redshaw, C., & Yamato, T. (2017). A pyrene-based approach to tune emission color from blue to yellow. Journal of Organic Chemistry, 82(14), 7176-7182. https://doi.org/10.1021/acs.joc.7b00685

The development of functionalized, luminescent, pyrene-based monomers has been and continues to be an area of great interest in terms of the design and fabrication of optical and electronic devices. Herein, a facile strategy to tune the emission colo... Read More about A pyrene-based approach to tune emission color from blue to yellow.

A 2-Styryl-1,8-naphthyridine derivative as a versatile fluorescent probe for the selective recognition of Hg²⁺, Ag⁺ and F⁻ ions by tuning the solvent (2017)
Journal Article
Wu, Y. T., Zhao, J.-L., Mu, L., Zeng, X., Wei, G., Redshaw, C., & Jin, Z. (2017). A 2-Styryl-1,8-naphthyridine derivative as a versatile fluorescent probe for the selective recognition of Hg²⁺, Ag⁺ and F⁻ ions by tuning the solvent. Sensors and actuators. B, Chemical, 252, 1089-1097. https://doi.org/10.1016/j.snb.2017.06.057

A novel fluorescent probe 1 has been synthesized by a microwave reaction, and its ion-binding and fluorescence-sensing properties have been investigated under different solvent conditions. The analysis results indicated that probe 1 can act as a mult... Read More about A 2-Styryl-1,8-naphthyridine derivative as a versatile fluorescent probe for the selective recognition of Hg²⁺, Ag⁺ and F⁻ ions by tuning the solvent.

Use of metal catalysts bearing Schiff base macrocycles for the ring opening polymerization (ROP) of cyclic esters (2017)
Journal Article
Redshaw, C. (2017). Use of metal catalysts bearing Schiff base macrocycles for the ring opening polymerization (ROP) of cyclic esters. Catalysts, 7(5), Article 165. https://doi.org/10.3390/catal7050165

© 2017 by the authors. Schiff base macrocycles are emerging as useful scaffolds for binding two or more catalytic metals in close proximity. Such coordination chemistry allows for the evaluation of potentially beneficial catalytic cooperative effects... Read More about Use of metal catalysts bearing Schiff base macrocycles for the ring opening polymerization (ROP) of cyclic esters.

A readily accessible multifunctional probe: simultaneous recognition of the cation ZN²⁺ and the anion F⁻ via distinguishable wavelengths (2017)
Journal Article
Zeng, L., Zhao, J. L., Mu, L., Zeng, X., Wei, G., Redshaw, C., & Jin, Z. (2017). A readily accessible multifunctional probe: simultaneous recognition of the cation ZN²⁺ and the anion F⁻ via distinguishable wavelengths. 880-01 Wu ji hua xue xue bao = Journal of inorganic chemistry, 33(5), 769-778. https://doi.org/10.11862/CJIC.2017.076

The probe 1 was readily prepared via condensation of 8-formyl-7-hydroxy-coumarin and carbonic dihydrazide in a one-step procedure. Probe 1 exhibited high sensitivity and selectivity towards Zn²⁺ and F⁻ through a “turn-on” fluorescence response and/or... Read More about A readily accessible multifunctional probe: simultaneous recognition of the cation ZN²⁺ and the anion F⁻ via distinguishable wavelengths.

Synthesis and fluorescence emission properties of D-π-D monomers based on dithieno[3,2-b:2′,3′-d]thiophene (2017)
Journal Article
Wang, C.-Z., Do, J.-H., Akther, T., Feng, X., Matsumoto, T., Tanaka, J., Redshaw, C., & Yamato, T. (2017). Synthesis and fluorescence emission properties of D-π-D monomers based on dithieno[3,2-b:2′,3′-d]thiophene. Journal of Luminescence, 188(388), 388-393. https://doi.org/10.1016/j.jlumin.2017.04.060

We herein present four highly fluorescent and stable D-π-D monomers (2), which were designed and synthesized using different types of aryl substituent as the donor via a Suzuki-Miyaura coupling reaction. We have studied these four symmetrical chromop... Read More about Synthesis and fluorescence emission properties of D-π-D monomers based on dithieno[3,2-b:2′,3′-d]thiophene.

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.-Q., Wang, X., Elsegood, M. R., Elsegood, M. R. J., Wang, X., Zhao, K.-Q., Al-Khafaji, Y., Mo, S., Prior, T., Elsegood, M., & 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 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., Thuery, P., Redshaw, C., & 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.

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., Redshaw, C., & 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.-B., Gao, Z.-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.-X., Ni, X.-L., Wei, G., & 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.-Z., 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.

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