Synthesis of Green Colored Photochromic 6′-Arylamino Spiro [2H]Naphth[1,2-b]oxazines

REFERENCES

• Lokshin , V. ; Samat , A. ; Metelitsa , A. V. Spirooxazines: Synthesis, structure, spectral and photochromic properties . Russ. Chem. Rev. 2002 , 71 , 893 – 916 .
   Google Scholar
• Bouas-Laurent , H. ; Durr , H. Organic photochromism . Pure Appl. Chem. 2001 , 73 , 639 – 665 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• Rickwood , M. ; Marsden , S. D. ; Askew , V. E. Photochromic spiroxazine compounds. U.S. Patent 5,446,150, Apr. 29, 1995 .
   Google Scholar
• Ercole , F. ; Davis , T. P. ; Evans , R. A. Comprehensive modulation of naphthopyran photochromism in a rigid host matrix by applying polymer conjugation . Macromolecules 2009 , 42 , 1500 – 1511 .
   Google Scholar
• 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.
   Google Scholar
• Such , G. K. ; Evans , R. A. ; Davis , T. P. The use of block copolymers to systematically modify photochromic behaviour . Macromolecules 2006 , 39 , 9562 – 9570 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Web of Science ®Google Scholar
• 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 .
   Google Scholar
• 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 .
   Web of Science ®Google Scholar
• Such , G. ; Evans , R. A. ; Davis , T. P. Control of photochromism through local environment effects using living radical polymerisation . Macromolecules 2004 , 37 , 9664 – 9666 .
   Google Scholar
• 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 .
   Google Scholar
• 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 .
   Google Scholar
• Arsenov , V. D. ; Gorelik , A. M. ; Strokach , Y. P. ; Barachevsky , B. A. ; Alfimov , M. V. 1-N-alkyl-5′-[(N′-(un)substituted)amido]spiroindolino naphthoxazines, their preparation, compositions and (co)polymer matrices containing them. European Patent 1044978, Oct. 18, 2000 .
   Google Scholar
• Armarego , W. L. F. ; Perrin , D. D. Purifcation of Laboratory Chemicals ; Butterworth Heinemann : Oxford , 1997 .
   Google Scholar
• 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 .
   Google Scholar