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Synthetic studies on macrocyclic materials

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Personal profile

Biography

Click here for a Retrosynthesis Tutorial. (This might be of some historical interest as it was one of the first web based interactive tutorials of its type! The associated lecture notes are also outdated presentationally!)

Click here for current PhD opportunities in CHE. But feel free to email me to discuss projects outside these areas and alternative sources of funding.

Andrew Cammidge gained a PhD in 1990 investigating some novel phthalocyanine liquid crystals and then spent just over a year at the University of Toledo, USA, working with Alan Morgan on the synthesis of novel organic chromophores for the photodynamic treatment of cancer. In 1991 he returned to the UK to a postdoctoral position at the University of Leeds, spending three years working with Neville Boden and Richard Bushby working on the development of novel syntheses and applications of discotic liquid crystals, before returning to UEA in 1995. He has been a Professor in Chemistry since 2011.

Currently he leads a research team working on synthesis and investigation of complex organic materials, teaches organic chemistry at all levels. He is Deputy Head of School, Director of Finance, Director of Admissions and Course Director for the School’s MSc in Advanced Organic Chemistry. Outside of UEA, he chairs the RSC research fund working group.

Selected Publications

Alkorbi, F., Díaz-Moscoso, A., Gretton, J., Chambrier, I., Tizzard, G. J., Coles, S. J., Hughes, D. L. & Cammidge, A. N., 29 Mar 2021.
Complementary syntheses giving access to a full suite of differentially substituted phthalocyanine-porphyrin hybrids.
In : Angewandte Chemie International Edition. 60, 14, p. 7632-7636 5 p.

Roy, P., Bressan, G., Gretton, J., Cammidge, A. N. & Meech, S. R., 3 May 2021.
Ultrafast excimer formation and solvent controlled symmetry breaking charge separation in the excitonically coupled subphthalocyanine dimer.
In : Angewandte Chemie International Edition. 60, 19, p. 10568-10572 5 p.

Gonzalez Lucas, D., Soobrattee, S., Hughes, D., Tizzard, G. J., Coles, S. J. & Cammidge, A., 21 Aug 2020.
Straightforward and controlled synthesis of porphyrin-phthalocyanine-porphyrin heteroleptic triple-decker assemblies.
In : Chemistry - A European Journal. 26, 47, p. 10724-10728 5 p.

 

Career

  • BSc UEA 1984-1987
  • PhD UEA 1987-1990
  • Postdoctoral fellow University of Toledo 1991-1992
  • Postdoctoral fellow University of Leeds 1992-1995
  • Lecturer UEA 1995-2001
  • Senior Lecturer UEA 2001-2005
  • Reader UEA 2005-2011
  • Professor UEA 2011-

External Activities

  • Chair of RSC Research Fund Working Group

Key Research Interests and Expertise

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.


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.

The group’s work benefits from wide and diverse collaborations with both fellow academics and industry.

Key Responsibilities

  • Professor of Organic Chemistry
  • Deputy Head of School of Chemistry
  • Director of Finance
  • Member Chemistry Executive
  • Course Director for Taught MSc in Advanced Organic Chemistry.

Specialisms

Synthesis of organic materials, specifically liquid crystals, polymers, organic chromophores such as porphyrins and phthalocyanines, novel catalysts and molecular imprinting.

Teaching Interests

Andrew Cammidge teaches across all organic chemistry, and currently lectures at second year (aromaticity, conformational analysis), third year (pericyclic reactions) and M-year (supramolecular chemistry) as well as occasional input to specialist modules (advanced topics, problem solving in organic chemistry).

Areas Of Expertise

SYNTHESIS||MACROCYCLES||LIQUID CRYSTALS||LIQUID CRYSTALS||MOLECULAR IMPRINTING||ORGANIC MATERIALS||POLYMERS||PHTHALOCYANINES||PORPHYRINS||TRIPHENYLENES||CROSS-COUPLING||SUPRAMOLECULAR CHEMISTRY||

Administrative Posts

Deputy Head of Chemistry

Research Group Membership

Current research co-workers:

Expertise related to UN Sustainable Devlopment Goals

In 2015, UN member states agreed to 17 global Sustainable Development Goals (SDGs) to end poverty, protect the planet and ensure prosperity for all. This person’s work contributes towards the following SDG(s):

  • SDG 3 - Good Health and Well-being

Network

Recent external collaboration on country/territory level. Dive into details by clicking on the dots or