Gabbutt, Christopher - Huddersfield University - Department of Chemistry and Chemical Engineering

个人简介

I am a Senior Research Fellow in the Department of Chemical and Biological Sciences. Prior to joining Huddersfield in August 2012 I have, over the last 21 years taught and researched in organic chemistry and held numerous administrative roles at the Universities of Central Lancashire (1991-1998), Hull (1998-2001) and Leeds (2001-2012). My teaching experience ranges widely across the subject and encompasses both fundamental and applied aspects of organic chemistry. I have as a result of my PhD (1987, CNAA) a long-standing research interest in heterocyclic chemistry, in particular the chemistry of benzopyrans and fused-ring derivatives. My research has developed several new methods to synthesise or to functionalise benzopyran-containing ring systems. Work on a wide variety of other heterocycles has also been undertaken. Concomitantly, research on photochromic heterocyclic compounds, in collaboration with industry, has been actively pursued since 1986 and has also produced many ‘firsts’. These include the discovery of the most intense colouring photochromic compounds – i.e. the amino-substituted spirooxazines, the controlled thermal fading of spirooxazines, the discovery of hyperchromic naphthopyrans and, more recently, the first dichroic naphthopyrans. Work on photochromic compounds has resulted in 16 patents. Molecules developed over the years have now been commercialised world-wide. Other materials chemistry-based projects, funded, by industry are currently underway.

研究领域

Aspects of benzopyran chemistry which have been extensively explored include: (i) Rearrangements of acylbenzopyranone derivatives initiated by acid or by addition of organolithium or organocuprate reagents. (ii) Ring and lateral directed lithiation and reductive lithiations of chromones, xanthones and xanthendiones. (iv) The synthesis and cycloadditions of benzopyrans possessing iso-condensed furan, thiophene and pyrrole rings. Current interests centre upon: Heterocyclic Materials Chemistry Photochromism of aryl-linked naphthopyrans; investigation of substituent and electron transmission effects in naphthopyrans. Synthesis of optical molecular switches based on di(heteroaryl)ethene motifs. Design and synthesis of multiply switchable photochromic systems. Atropisomerism in photochromic compounds. Synthesis of novel p-deficient heterocyclic electron acceptors. Synthesis and properties of electrochromic compounds. Synthetic Heterocyclic Chemistry Synthesis of fused ring derivatives of 2H-pyran especially chromones, thiochromones and tetrahydroxanthendiones. Cycloaddition chemistry of furobenzopyrans. Synthesis of hetero-fused benzo[b]thiophenes and dibenzothiophenes. New routes to and applications of transition metal-mediated transformations (Pd, Ir and Rh) for the synthesis of novel functional organic materials. Synthesis of fused-ring siloles and azaindolizines.

近期论文

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Gentili, P., Rightler, A., Heron, B. and Gabbutt, C. (2015) ‘Extending Human Perception of Electromagnetic Radiation to the UV Region through Biologically Inspired Photochromic Fuzzy Logic (BIPFUL) Systems.’ Chemical Communications . ISSN 1359-7345 Aiken, S., Armitage, B., Gabbutt, C. and Heron, B. (2015) ‘An intramolecular, Pd-mediated alpha-arylation route to 4-aryl-2-naphthols’ Tetrahedron Letters , 56 (33), pp. 4840-4842. ISSN 0040-4039 Aiken, S., Crossley, D., Gabbutt, C., Heron, B., Biver, C., Archambeau, S. and Berit-Debat, F.(2015) Electrochromic two-core viologen derivatives and optical articles containing them. WO2015040031. Aiken, S., Gabbutt, C., Heron, B., Biver, C., Archambeau, S., Berit-Debat, F. and Duluard, S.(2015) Electrochromic single and two-core viologen derivatives and optical articles containing them. WO2015040033. Aiken, S., Gabbutt, C., Heron, B. and Kolla, S. (2015) ‘Photochromic bi-naphthopyrans’ Dyes and Pigments , 113, pp. 239-250. ISSN 0143-7208 Aiken, S., Allsopp, B., Booth, K., Gabbutt, C. and Heron, B. (2014) ‘5-Hydroxy substituted naphthofurans and naphthothiazoles as precursors of photochromic benzochromenes’ Tetrahedron , 70 (49), pp. 9352-9358. ISSN 0040-4020 Aiken, S., Booth, K., Gabbutt, C., Heron, B., Rice, C., Charaf-Eddin, A. and Jacquemin, D. (2014) ‘The first structural and spectroscopic characterisation of a ring-opened form of a 2H-naphtho[1,2-b]pyran: a novel photomerocyanine’ Chemical Communications , 50 (58), pp. 7900-7903. ISSN 1359-7345 Aiken, S., Gabbutt, C., Gillie, L., Heywood, J., Jacquemin, D., Rice, C. and Heron, B. (2013) ‘The Remarkable Hyperchromicity of Ketohydrazone Dyes and Pigment Lakes Derived from 4-Morpholino-2-naphthol’ European Journal of Organic Chemistry , 2013 (36), pp. 8097-8107. ISSN 1434-193X Chaitanya, K., Hai Ju, X., Heron, B. and Gabbutt, C. (2013) ‘Vibrational spectra and static vibrational contribution to first hyperpolarizability of naphthopyrans — A combined experimental and DFT study.’ Vibrational Spectroscopy , 69, pp. 65-83. ISSN 09242031 Aiken, S., Clayton, D., Gabbutt, C., Heron, B. and Kolla, S. (2013) ‘Cationic merocyanine dyes by photomodulation of [4-(naphthopyran-3-yl)phenyl]methines’ Dyes and Pigments , 97 (1), pp. 118-123. ISSN 0143-7208 Blackwell, C., Gabbutt, C., Guthrie, J. and Heron, B. (2012) ‘The synthesis and properties of vinyl substituted naphthopyrans and their styrene copolymers’ Dyes and Pigments , 95 (2), pp. 408-420. ISSN 0143-7208 Crossley, D., Gabbutt, C., Heron, B., Kay, P. and Mogstad, M. (2012) ‘Synthesis and photochromic properties of spiro[naphthopyran-7?H-benzocyclohepta-5?,8?-dienes]’ Dyes and Pigments , 95 (1), pp. 62-68. ISSN 0143-7208 Gabbutt, C., Heron, B., Kilner, C. and Kolla, S. (2012) ‘The synthesis and properties of naphthopyran– boradiazaindacene conjugates’ Dyes and Pigments , 94 (2), pp. 175-182. ISSN 0143-7208 Gabbutt, C., Gibbons, L., Heron, B. and Kolla, S. (2012) ‘The intramolecular capture of thermally generated merocyanine dyes derived from naphthopyrans: Photochromism of 5-(diarylhydroxymethyl)-2H-naphtho[1,2-b]pyrans’ Dyes and Pigments , 92 (3), pp. 995-1004. ISSN 0143-7208 Gabbutt, C., Heron, B., Kilner, C. and Kolla, S. (2012) ‘The synthesis and photochromism of a 2,2-diaryl-6-styryl-2H-[1]benzopyran: Unexpected palladium-mediated ring-contraction of a 6-bromo-2,2-diaryl-2H-[1]benzopyran’ Dyes and Pigments , 92 (2), pp. 825-830. ISSN 0143-7208 Chaitanya, K., Santhamma, C., Heron, B., Gabbutt, C. and Instone, A. (2011) ‘Vibrational assignment of the spectral data and thermodynamic properties of 2-chloro-4-fluorobenzophenone using DFT quantum chemical calculations’ Vibrational Spectroscopy , 57 (1), pp. 35-41. ISSN 0924-2031 Gabbutt, C., Heron, B., Kilner, C. and Kolla, S. (2011) ‘Hexatriene formation from the regiospecific alkene cross-metathesis of trans-1-(buta-1,3-dien-1-yl)-2-acryloyloxynaphthalene’ Journal of chemical research , 35 (9), pp. 531-535. ISSN 1747-5198 Curtis, A., Gabbutt, C., Heron, B. and Kilner, C. (2011) ‘Direct formation of ?,?-unsaturated dithioacetals from diarylpropynols’ Tetrahedron Letters , 52 (6), pp. 708-710. ISSN 0040-4039 Gabbutt, C., Heron, B., Kilner, C. and Kolla, S. (2010) ‘Benzopentalenonaphthalenones from the intramolecular capture of a merocyanine derived from a naphthopyran’ Chemical Communications , 46 (44), pp. 8481-8483. ISSN 1359-7345 Gabbutt, C., Heron, B., Kilner, C. and Kolla, S. (2010) ‘The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans’ Organic & Biomolecular Chemistry , 8 (21), pp. 4874-4883. ISSN 1477-0520