Convenient, Microwave-Assisted, One-Pot Synthesis of Photochromic Fulgimides Bearing Reactive Groups

REFERENCES

• Fan , M. G. ; Yu , L. H. ; Zhao , W. Fulgide family compounds: Synthesis, photochromism, and applications ; In Organic Photochromic and Thermochromic Compounds, Main Photochromic Families ; J. C. Crano , R. J. Guglielmetti (Eds.); Kluwer Academic Publishers : New York , 2002 ; vol. 1 , pp. 141 – 206 .
   Google Scholar
• Yokoyama , Y. Fulgides for memories and switches . Chem. Rev. 2000 , 100 , 1717 – 1739 .
   PubMed Web of Science ®Google Scholar
• Barachevsky , V. A. Photonics of organic photochromic systems: Modern trends . J. Photochem. Photobiol. A: Chem. 2008 , 196 , 180 – 189 .
   Web of Science ®Google Scholar
• Thomas , C. J. ; Wolak , M. A. ; Birge , R. R. ; Lees , W. J. Tuning the optical properties of fluorinated indolylfulgimides . J. Org. Chem. 2003 , 68 , 319 – 326 .
   PubMed Web of Science ®Google Scholar
• Matsushima , R. ; Sakaguchi , H. Comparison of the photochromic properties of fulgides and fulgimides . J. Photochem. Photobiol. A: Chem. 1997 , 108 , 239 – 245 .
   Web of Science ®Google Scholar
• Matsushima , R. ; Nishiyama , M. ; Doi , M. Improvements in the fatigue resistances of photochromic compounds . J. Photochem. Photobiol. A: Chem. 2001 , 139 , 63 – 69 .
   Web of Science ®Google Scholar
• Nagoh , H. ; Momda , J. ; Tanizawa , T. Fulgimide compound and use thereof and composition containing said compound . US Patent 006110400A , 2000 .
   Google Scholar
• Heller , H. G. Derivatives of fulgimide . GB Patent 1271655 , 1972 .
   Google Scholar
• Glaze , A. P. ; Heller , H. G. ; Whittall , J. Photochromic heterocyclic fulgides, Part 7: (E)-Adamantylidene-[1-(2,5-dimethyl-3-furyl)ethylidene succinic anhydride and derivatives: Model photochromic compounds for optical recording media . J. Chem. Soc. Perkin Trans. 2 1992 , 591 – 594 .
   Google Scholar
• Heller , H. G. ; Megit , R. M. Overcrowded molecules, part XI: Fatigue-free photochromic systems involving (E)-2-isopropylidene-3-(mesitylmethylene)succinic anhydride and N-phenylimide . J. Chem. Soc., Perkin Trans. 1 1974 , 923 – 927 .
   Google Scholar
• Darcy , P. J. ; Heller , H. G. ; Patharakorn , S. ; Piggott , R. D. ; Whittall , J. Photochromic systems, part 1: Photochemical studies on (E)-2-isopropylidene-3-[l-(3,4,5-trimethoxyphenyl)ethylidene]succinic anhydride and related compounds . J. Chem. Soc., Perkin Trans. 1 1986 , 315 – 319 .
   Google Scholar
• Liang , Y. ; Dvornikov , A. S. ; Rentzepis , P. M. A novel non-destructible readout molecular memory . Opt. Commun. 2003 , 223 , 61 – 66 .
   Web of Science ®Google Scholar
• Dvornikov , A. S. ; Liang , Y. ; Cruse , C. S. ; Rentzepis , P. M. Spectroscopy and kinetics of a molecular memory with nondestructive readout for use in 2D and 3D storage systems . J. Phys. Chem. B 2004 , 108 , 8652
   Web of Science ®Google Scholar
• Li , X. L. ; Pang , S. C. ; Xu , X. M. ; Chen , H. Photochromic reactive dyes and their preparation . CN Patent 101134849A , 2007 (in Chinese) .
   Google Scholar
• Iwamoto , O. ; Sugiyama , H. ; Hara , T. Fulgimide derivatives . EPPaten 420397A1 , 1990 .
   Google Scholar
• Cabrera , I. ; Dittrich , A. ; Ringsdorf , H. Thermally irreversible photochromic liquid crystal polymers . Angew. Chem., Int. Ed. Engl. 1991 , 30 , 76 – 78 .
   Web of Science ®Google Scholar
• Willner , I. ; Rubin , S. ; Wonner , J. ; Effenberger , F. ; Bauerle , P. ; Effenberger , P. ; Bauerle , J. Photoswitchable binding of substrates to proteins: Photoregulated binding of α-d-mannopyraose to concanavalin a modified by a thiophenefulgide dye . J. Am. Chem. Soc. 1992 , 114 , 3150 – 3151 .
   Web of Science ®Google Scholar
• Willner , I. ; Lion-Dagan , M. ; Rubin , S. ; Wonner , J. ; Effenberger , F. ; Bauerle , P. Photoregulation of α-chymotrypsin activity in organic media: Effects of bioimprinting . Photochem. Photobiol. 1994 , 59 , 491 – 496 .
   PubMed Web of Science ®Google Scholar
• Tanizawa , T. ; Kobayakawa , T. Fulgimide compound . US Patent 005631382A , 1997 .
   Google Scholar
• Okumyama , T. ; Yokoyama , Y. Control of the association of indolylfulgimide with bis(acylamino)pyridine by photochromism . Bull. Chem. Soc. Jpn. 2001 , 74 , 2181 – 2187 .
   Web of Science ®Google Scholar
• Liang , Y. C. ; Dvornikov , A. S. ; Rentzepis , P. M. Synthesis of novel photochromic fluorescing 2-indolylfulgimides . Tetrahedron Lett. 1999 , 40 , 8067 – 8069 .
   Web of Science ®Google Scholar
• Liang , Y. C. ; Dvornikov , A. S. ; Rentzepis , P. M. Synthesis and photochemistry of photochromic fluorescing indol-2-ylfulgimides. J. Mat. Chem. 2000, 10, 2477–2482.
   Web of Science ®Google Scholar
• Otto , B. ; Ruck-Braun , K. Syntheses and UV/vis properties of amino-functionalized fulgimides . Eur. J. Org. Chem. 2003 , 2409 – 2417 .
   Web of Science ®Google Scholar
• Li , X. L. ; Xu , X. M. ; Chen , H. ; Liu , S. Y. Synthesis and photochromism of asymmetric bis-photochromophoric compounds . Chin. J. Org. Chem. 2005 , 25 ( Suppl. 2 ), 624 .
   Google Scholar
• Lidstrom , P. ; Tierney , J. ; Wathey , B. ; Westman , J. Microwave assisted organic synthesis—A review . Tetrahdron 2001 , 57 , 9225 – 9283 .
   Web of Science ®Google Scholar
• Eycken , E. V. ; Kappe , C. O. (Eds.); Microwave-Assisted Synthesis of Heterocycles, Topics in Heterocyclic Chemistry ; Spinger-Verlag : Berlin , 2006 .
   Google Scholar
• Larhed , M. ; Olofsson , K. (Eds.); Microwave Methods in Organic Synthesis, Topics in Current Chemistry ; Spinger-Verlag : Berlin , 2006 .
   Google Scholar
• Dallinger , D. ; Kappe , C. O. Microwave-assisted synthesis in water as solvent . Chem.Rev. 2007 , 107 , 2563 – 2591 .
   PubMed Web of Science ®Google Scholar
• Seijas , J. A. ; Vázquez-Tato , M. P. ; Martínez , M. M. ; Núñez-Corredoira , G. Direct synthesis of imides from dicarboxylic acids using microwaves . J. Chem. Res. Synop. 1999 , 420 – 421 .
   Web of Science ®Google Scholar
• Hijji , Y. M. ; Benjamin , E. Efficient microwave assisted syntheses of unsubstituted cyclic imides . Heterocycles 2006 , 68 , 2259 – 2267 .
   Web of Science ®Google Scholar
• Borah , H. N. ; Boruah , R. C. ; Sandhu , J. S. Microwave-induced one-pot synthesis of N-carboxyalkyl maleimides and phthalimides . J. Chem. Res. 1998 , 8 , 272 – 273 .
   Web of Science ®Google Scholar
• Vidal , T. ; Petit , A. ; Loupya , A. ; Gedyeb , R. N. Re-examination of microwave-induced synthesis of phthalimides . Tetrahedron 2000 , 56 , 5473 – 5478 .
   Web of Science ®Google Scholar
• Martin , B. ; Sekljic , H. ; Chassaing , C. Microwave-assisted solid-phase synthesis of phthalimides . Org. Lett. 2003 , 5 , 1851 – 1853 .
   PubMed Web of Science ®Google Scholar
• Mortoni , A. ; Martinelli , M. ; Piarulli , U. ; Regalia , N. ; Gagliardi , S. Microwave-assisted solvent-free synthesis of a quinoline-3,4-dicarboximid library on inorganic solid supports . Tetrahedron Lett 2004 , 45 , 6623 – 6627 .
   Web of Science ®Google Scholar
• Lee , W. W. ; Ganb , L. M. ; Loh , T. P. Microwave-assisted synthesis of photochromic fulgimides . J. Photochem. Photobiol. A: Chem. 2007 , 185 , 106 – 109 .
   Web of Science ®Google Scholar
• Li , C. X. ; Ke , Y. K. Photochromic indylanhydride synthesis and properties (E)-1-benzyl-2-methy-3-indylethylidene succinic anhydride . J. Beijing Univ. Chem. Tech. 1999 , 25 , 71 – 76 .
   Google Scholar
• Yu , L. H. ; Ming , Y. F. ; Fan , M. G. Synthesis and photochromism of aryl substituted fulgides . Chin. J. Chem. 1996 , 54 , 716 – 721 .
   Google Scholar
• Chen , Y. ; Li , T. K. ; Fan , M. G. ; Mai , X. S. ; Zhao , H. ; Xu , D. Y. Photochromic fulgide for multi-level recording . Mater. Sci. Eng. B 2005 , 123 , 53 – 56 .
   Web of Science ®Google Scholar
• Kose , M. ; Orhan , E. ; Buyukgungor , O. Synthesis of novel photochromic methyl cyanoacetate- condensed fulgide derivatives . J. Photochem. Photobiol. A: Chem. 2007 , 18 , 358 – 363 .
   Web of Science ®Google Scholar
• Thomas , C. J. ; Wolak , M. A. ; Birge , R. R. ; Lees , W. J. Improved synthesis of indolyl fulgides . J. Org. Chem. 2001 , 66 , 1914 – 1918 .
   PubMed Web of Science ®Google Scholar
• Wolak , M. A. ; Gillespie , N. B. ; Thomas , C. J. ; Birge , R. R. ; Lees , W. J. Optical and thermal properties of photochromic fluorinated adamantylidene indolylfulgides . J. Photochem. Photobiol. A: Chem. 2002 , 147 , 39 – 44 .
   Web of Science ®Google Scholar