Synthesis of green colored photochromic 6'-arylamino spiro [2H]naphth[1,2-b]oxazines

Synthetic Communications

Volumn 40, Issue 24, 2010, Pages 3618-3628

  York, Mark ^a   Evans, Richard A ^a  

^a CSIRO   (Australia)

Author keywords

Photochromic; photochromism; spirooxazine

Indexed keywords

1,2 NAPHTHOQUINONE DERIVATIVE; AMINE; NAPHTHOXAZINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 78149416924     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903457423     Document Type: Article

References (18)

1. Lokshin, V.; Samat, A.; Metelitsa, A. V. Spirooxazines: Synthesis, structure, spectral and photochromic properties. Russ. Chem. Rev. 2002, 71, 893-916.
2. Bouas-Laurent, H.; Durr, H. Organic photochromism. Pure Appl. Chem. 2001, 73, 639-665.
3. Clarke, D. A.; Heron, B. M.; Gabbutt, C. D.; Hepworth, J. D.; Partington, S. M.; Corns, S. N. Photochromic compounds. U.S. Patent 6,303,673, Oct. 16, 2001.
4. Rickwood, M.; Marsden, S. D.; Askew, V. E. Photochromic spiroxazine compounds. U.S. Patent 5,446,150, Apr. 29, 1995.
5. Ercole, F.; Davis, T. P.; Evans, R. A. Comprehensive modulation of naphthopyran photo-chromism in a rigid host matrix by applying polymer conjugation. Macromolecules 2009, 42, 1500-1511.
6. Malic, N.; Campbell, J. A.; Evans, R. A. Superior photochromic performance of napthopyrans in a rigid host matrix using polymer conjugation: Fast, dark and tuneable. Macromolecules 2008, 41, 1206-1214.
7. Such, G. K.; Evans, R. A.; Davis, T. P. The use of block copolymers to systematically modify photochromic behaviour. Macromolecules 2006, 39, 9562-9570.
8. Malic, N.; Evans, R. A. Synthesis of carboxylic acid and ester mid-functionalized polymers using RAFT polymerization and ATRP. Aust. J. Chem. 2006, 59, 763-771.
9. Such, G. K.; Evans, R. A.; Davis, T. P. Rapid photochromic switching in a rigid polymer matrix using living radical polymerisation (ATRP). Macromolecules 2006, 39, 1391-1396.
10. Evans, R. A.; Such, G. K. Research trends in photochromism: Control of photochromism in rigid polymer matrices and other advances. Aust. J. Chem. 2005, 58, 825-830.
11. Evans, R. A.; Hanley, T. L.; Skidmore, M. A.; Davis, T. P.; Such, G. K.; Yee, L. H.; Ball, G. E.; Lewis, D. A. The generic enhancement of photochromic dye switching speeds in rigid polymer matrices. Nat. Mater. 2005, 4, 294-253.
12. Such, G. K.; Evans, R. A.; Davis, T. P. Tailoring photochromic performance of polymer-dye conjugates using living radical polymerization (ATRP). Liq. Cryst. Mol. Cryst. 2005, 430, 273-279.
13. Such, G.; Evans, R. A.; Davis, T. P. Control of photochromism through local environment effects using living radical polymerisation. Macromolecules 2004, 37, 9664-9666.
14. Such, G.; Evans, R. A.; Yee, L. H.; Davis, T. P. Factors influencing photochromism of spiro-compounds with polymeric matrices. J. Macromol. Sci. Part C Polymer Reviews 2003, C43, 547.
15. Yoshida, K.; Koujiri, T.; Oga, N.; Ishiguro, M.; Kubo, Y. The effect of metal chelate complexation on the reactivity and absorption spectra of 1,2-naphthoquinones: The synthesis of new types of near i.r. absorbing dyes. J. Chem. Soc., Chem. Commun. 1989, 708-710
16. 0-[(N'-(un)substituted)amido]spiroindolino naphthoxazines, their preparation, compositions and (co)polymer matrices containing them. European Patent 1044978, Oct. 18, 2000.
17. Armarego, W. L. F.; Perrin, D. D. Purifcation of Laboratory Chemicals; Butterworth Heinemann: Oxford, 1997.
18. Ooyama, Y.; Nagano, S.; Okamura, M.; Yoshida, K. Solid-State Fluorescence changes of 2-(4-cyanophenyl)-5-[4-(diethylamino)-phenyl]-3H-imidazo[4,5-a] naphthalene upon inclusion of organic solvent molecules. Eur. J. Org. Chem. 2008, 5899-5906.