화학공학소재연구정보센터
Macromolecular Research, Vol.12, No.5, 493-500, October, 2004
Transient Protection of Intramolecular Hydrogen Bonding: A Simple but Elegant Approach for Functional Imaging
E-mail:
We have developed a novel method for patterning functional images in thin polymer films. The key materials we utilized for the imaging were dihydroxyanthraquinones protected with acid-labile tert-butoxycarbonyl (t-Boc) blocking groups. Among the tested compounds, 1,4-dihydroxyanthraquinone (quinizarin; 1) underwent the most drastic change in terms of its color and fluorescence upon protection. We prepared the t-Boc-protected quinizarin and polymers bearing the protected quinizarins as pendent groups. To investigate the possibility of a single-component imaging system, we synthesized a styrenic monomer 14 incorporating protected quinizarin and a maleimide derivative 15 bearing a photoacid generating group and subjected them to polymerization. Selective removal of the protecting groups of the quinizarin moieties in the exposed area using photolithographic techniques allowed regeneration of quinizarin and patterned fluorescence images in the polymer films.
  1. Vekselmen AM, Zhang C, Darling GD, Chem. Mater., 9, 1942 (1997) 
  2. Zhang C, Vekselman AM, Darling GD, Chem. Mater., 7, 850 (1995) 
  3. Schilling ML, Katz HE, Houlihan FM, Kometani JM, Stein SM, Nalamasu O, Macromolecules, 28(1), 110 (1995) 
  4. Kim JM, Chang TE, Park RH, Kim DJ, Han DK, Ahn KD, Chem. Lett., 712 (2000) 
  5. Frechet JMJ, Eichler E, Ito H, Willson CG, Polymer, 24, 995 (1983) 
  6. Reichmanis E, Houlihan FM, Nalamasu O, Neenan TX, Chem. Mater., 3, 394 (1991) 
  7. Macdonal SA, Willson CG, Frechet JMJ, Accounts Chem. Res., 27, 151 (1994) 
  8. Niu QJ, Frechet JMJ, Angew. Chem.-Int. Edit., 37, 667 (1998) 
  9. Chung CM, Ahn KD, React. Funct. Polym., 40(1), 1 (1999) 
  10. Kim JM, Chang TE, Kang JH, Han DK, Ahn KD, Adv. Mater., 11, 1499 (1999) 
  11. Kim JM, Chang TE, Kang JH, Park KH, Han DK, Ahn KD, Angew. Chem.-Int. Edit., 39, 1780 (2000) 
  12. Kim JM, Kang JM, Han Dk, Lee CW, Ahn KD, Chem. Mater., 10, 2332 (1998) 
  13. Lee JH, Cho I, Ahn KD, Kim JM, Chem. Lett., 716 (2001) 
  14. Kim S, Park SY, Adv. Mater., 15, 1341 (2003) 
  15. Pistolis G, Boyatzis S, Chatzichristidi M, Argitis P, Chem. Mater., 14, 790 (2002) 
  16. Lee CW, Yuan Z, Ahn KD, Lee SH, Chem. Mater., 14, 4572 (2002) 
  17. Coenjarts C, Garcia O, Llauger L, Palfreyman J, Vinette AL, Scaiano JC, J. Am. Chem. Soc., 125(3), 620 (2003) 
  18. Yang NC, Choi HW, Lee JK, Hwang JI, Suh DH, Chem. Lett., 824 (2002) 
  19. Ahn KD, Chung Cm, Koo DI, Chem. Mater., 6, 1452 (1994) 
  20. Kim ST, Kim JB, Kim JM, Chung CM, Ahn KD, J. Photopolym. Sci. Tech., 10, 489 (1997)