研究领域
My group aims to combine purely curiosity-driven research with the tackling of some specific challenges facing modern chemical sciences development. My main research interests and activities concern transition-metal catalysis and molecular (supramolecular) materials. Indeed many projects combine these two themes and use catalysis to access new materials. For example, as part of a project aimed at synthesis of chiral biphenyls for use as liquid crystal dopants, we invented and reported the first intermolecular asymmetric Suzuki-Miyaura cross-coupling reaction. Probing the reaction allowed us to unravel the mechanism and inform design and optimization of cross-coupling catalysis. This work has challenged the accepted key steps of the cross-coupling cycle, and we have described an alternative mechanism that operates when challenging substrates are employed. With this information we were able to transfer efficient catalysis from homogeneous to heterogeneous conditions using, for the first time, the principle of molecular imprinting. Cross-coupling chemistry remains under investigation in the group.
In most of our research, however, the molecules and molecular materials themselves are the main focus. We design and molecules that will assemble themselves into higher order, more complex structures, either spontaneously or under a chemical influence (reaction). The group has much experience in the field of discotic liquid crystalline systems based on triphenylene cores. The early focus of our work in this area was to develop new syntheses of symmetrical and unsymmetrical triphenylenes in order to understand structural features governing the type and stability of the mesophases they form. Most recently our work has investigated flat, conjugated twinned systems with formally antiaromatic character. Stable dehydroannulene structures are produced by twinning the triphenylenes through their 3,6-positions – an arrangement that maintains conjugation but prevents decomposition through pericyclic pathways. The materials prove to be particularly interesting because they show thermotropic nematic liquid crystal phases and in the solid state show pi-overlap in 2-dimensions with each twin bridging two triphenylene columns. The latest work has extended this initial finding by targeting redox-active twins linked through pyrrole and thiophene units to give expanded porphyrinoid structures.
The second major research area revolves around macrocyclic chromophores based on porphyins and phthalocyanines. Phthalocyanines in particular are also known for their discotic liquid crystal behavior and the group has made significant contributions in this area. However, in most of our research the liquid crystal properties of new materials is not the overriding driving force, rather it is the investigation of fundamentally new architectures for application in diverse molecular electronic devices. Within these projects we design ambitious targets – “molecular machines” that resemble well-known macroscopic structures, but whose molecular variant can do work or function in an advanced technology application.
Cartoon depictions of such a machine (based on the fairground “Teacups” ride) are shown in the box. Construction of such machines presents new synthesis challenges, and again we invent new chemistry to achieve the goals. For example, the group has developed, and now reported, straightforward syntheses of phthalocyanine analogues where 1-4 of the meso-nitrogen atoms are replaced by methine fragments to give porphyrin-phthalocyanine hybrids. The parent compounds themselves have been known for some time but the area has been neglected because of the difficulties associated with their synthesis. Our single step procedure to a wide variety of substituted derivatives will open the way for further investigation. Already it is becoming apparent that the hybrid materials offer advantages over their phthalocyanine cousins in terms of their optoelectronic performance. A major breakthrough has delivered the first efficient, controlled synthesis of single hybrid species, opening the way for development of these new classes of organic material. The chemistry developed opens up further potential for new and exciting research and materials design.
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Managa, M., Mack, J., Gonzalez Lucas, D., Remiro Buenamanana, S., Tshangana, C., Cammidge, A., Nyokong, T.(2016)Photophysical properties of tetraphenylporphyrinsubphthalocyanine conjugatesin Journal of Porphyrins and Phthalocyanines20. Full Text UEA Repository(Article)
Cammidge, A., Obi, G., Turner, R., Coles, S. J., Tizzard, G. J.(2015)The synthesis of unsymmetrically substituted triphenylenes through controlled construction of the core and subsequent aromatic substitution reactions – a perspective and updatein Liquid Crystals42.pp. 819-825 Full Text UEA Repository(Article)
Chaure, N. B., Cammidge, A. N., Chambrier, I., Cook, M. J., Ray, A.(2015)A Tetrabenzotriazaporphyrin Based Organic Thin Film Transistor: Comparison with a Device of the Phthalocyanine Analoguein ECS Journal of Solid State Science and Technology4.pp. 3086-3090 Full Text UEA Repository(Article)
Alharbi, N., Tizzard, G. J., Coles, S. J., Cook, M., Cammidge, A.(2015)First Examples of Functionalisation of Meso-Aryl Tetrabenzotriazaporphyrins (TBTAPs) Through Cross-Coupling Reactionsin Tetrahedron71.pp. 7227–7232 Full Text UEA Repository(Article)
Garland, A., Chambrier, I., Cammidge, A., Cook, M.(2015)Design and synthesis of liquid crystalline phthalocyanines: combinations of substituents that promote the discotic nematic mesophasein Tetrahedron71.pp. 7310–7314 Full Text UEA Repository(Article)
Remiro Buenamanana, S., Diaz-Moscoso, A., Hughes, D., Bochmann, M., Tizzard, G. J., Coles, S. J., Cammidge, A.(2015)Synthesis of Meso-Substituted Subphthalocyanine-Subporphyrin Hybrids: Boron SubTriBenzoDiAzaPorphyrins (SubTBDAPs)in Angewandte Chemie-International Edition54.pp. 7510-7514 Full Text UEA Repository(Article)
Xiao, W., He, Z., Remiro Buenamanana, S., Turner, R., Xu, M., Yang, X., Jing, X., Cammidge, A.(2015)A π-Extended Donor-Acceptor-Donor Triphenylene Twin linked via a Pyrazine-bridgein Organic Letters17.pp. 3286–3289 Full Text UEA Repository(Article)
Chambrier, I., Banerjee, C., Remiro-Buenamañana, S., Chao, Y., Cammidge, A. N., Bochmann, M.(2015)Synthesis of Porphyrin–CdSe Quantum Dot Assemblies: Controlling Ligand Binding by Substituent Effectsin Inorganic Chemistry54.pp. 7368–7380 Full Text UEA Repository(Article)
Khozaee, Z., Sosa Vargas, L., Cammidge, A. N., Cook, M. J., Ray, A. K.(2015)Hybrid phthalocyanine/lead sulphide nanocomposite for bistable memory switchesin Materials Research Express2. Full Text UEA Repository(Article)
Diaz-Moscoso, A., Emond, E., Hughes, D. L., Tizzard, G. J., Coles, S. J., Cammidge, A. N.(2014)Synthesis of a Class of Core-Modified Aza-BODIPY Derivativesin The Journal of Organic Chemistry79.pp. 8932-8936 Full Text UEA Repository(Article)
Alharbi, N., Diaz-Moscoso, A., Tizzard, G. J., Coles, S. J., Cook, M. J., Cammidge, A. N.(2014)Improved syntheses of meso-aryl tetrabenzotriazaporphyrins (TBTAPs)in Tetrahedron70.pp. 7370-7379 Full Text UEA Repository(Article)
Garland, A., Bryant, G., Cambrier, I., Cammidge, A., Cook, M.(2014)Liquid crystalline properties of unsymmetrically substituted phthalocyanines: structural features leading to nematic mesophase materialsin Journal of Porphyrins and Phthalocyanines18.pp. 944-949 Full Text UEA Repository(Article)
Gopee, H., Cammidge, A. N., Oganesyan, V. S.(2013)Probing Columnar Discotic Liquid Crystals by EPR Spectroscopy with a Rigid-Core Nitroxide Spin Probein Angewandte Chemie International Edition52.pp. 8917-8920 Full Text UEA Repository(Article)
Pal, C., Sharma, A. K., Cammidge, A. N., Cook, M. J., Ray, A. K.(2013)Octaoctyl-Substituted Lutetium Bisphthalocyanine for NADH Biosensingin The Journal of Physical Chemistry B117.pp. 15033–15040 Full Text UEA Repository(Article)
Chaure, N. B., Barard, S., Ray, A. K., Cammidge, A. N., Cook, M. J.(2013)Ambipolar charge transport in non-peripherally substituted octahexyl zinc phthalocyaninein EPL (Europhysics Letters)104. Full Text UEA Repository(Article)
Díaz-moscoso, A., Tizzard, G. J., Coles, S. J., Cammidge, A. N.(2013)Synthesis of meso-Substituted Tetrabenzotriazaporphyrins: Easy Access to Hybrid Macrocyclesin Angewandte Chemie International Edition52.pp. 10784-10787 Full Text UEA Repository(Article)
Gopee, H., Kong, X., He, Z., Chambrier, I., Hughes, D. L., Tizzard, G. J., Coles, S. J., Cammidge, A. N.(2013)Expanded Porphyrin-like Structures Based on Twinned Triphenylenesin Journal of Organic Chemistry78.pp. 9505-9511 Full Text UEA Repository(Article)
Heeney, M. J., Al-raqa, S. A., Auger, A., Burnham, P. M., Cammidge, A. N., Chambrier, I., Cook, M. J.(2013)Routes to some 3,6-disubstituted phthalonitriles and examples of phthalocyanines derived therefrom: An overviewin Journal of Porphyrins and Phthalocyanines17.pp. 649-664 Full Text UEA Repository(Article)
Sosa-vargas, L. X., Chambrier, I., Macdonald, C. J., Coles, S. J., Tizzard, G. J., Cammidge, A. N., Cook, M. J.(2013)Synthesis and characterization of some octaalkyl substituted lead phthalocyanines and unexpected variations in lead lability arising from the position of substituents and their chain lengthin Journal of Porphyrins and Phthalocyanines17.pp. 511-521 Full Text UEA Repository(Article)
Mckenzie, I., Cammidge, A., Gopee, H., Dilger, H., Scheuermann, R., Stoykov, A., Jayasooriya, U.(2013)Muoniated spin probes in the discotic liquid crystal HHTT: Rapid electron spin relaxation in the hexagonal columnar and isotropic phasesin Physical Review E87. Full Text UEA Repository(Article)
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