Macroporous poly(aromatic amine): Synthesis and film fabrication

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 354, Issue 1-3, 2010, Pages 156-161

  Hill, Jonathan P ^a   Lee, Michael V ^a   Yu, Xiao Yan ^a   Okamoto, Ken ^a   Linford, Mathew R ^b   Ariga, Katsuhiko ^a  

^a NATIONAL INSTITUTE FOR MATERIALS SCIENCE   (Japan)

^b Brigham Young University   (United States)

Author keywords

Aromatic amine; Breath figure; Honeycomb film; Macroporous; Polymer

Indexed keywords

AMINES; HONEYCOMB STRUCTURES; SYNTHESIS (CHEMICAL);

AROMATIC AMINES; BREATH FIGURES; DIAMINONAPHTHALENE; FILM FABRICATION; HOLE SIZE; HONEYCOMB FILMS; MACRO-POROUS FILMS; MACROPOROUS; MACROPOROUS POLYMERS; MICRO-PARTICLES; ORDERED MACROPOROUS; SOLUBLE POLYMERS;

AROMATIC POLYMERS;

1H,2H DIHYROPERIMIDINE DERIVATIVE; ALDEHYDE; AROMATIC AMINE; CHEMICAL COMPOUND; MONOMER; NANOFIBER; POLY(1,8 DIAMINONAPHTHALENE); POLY(AROMATIC AMINE); POLYMER; UNCLASSIFIED DRUG;

ARTICLE; BIOFILM; CATALYST; CHEMICAL STRUCTURE; MEMBRANE MICROPARTICLE; NANOFABRICATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 73049115968     PISSN: 09277757     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.colsurfa.2009.07.033     Document Type: Article

References (119)

1. Canham L.T. Appl. Phys. Lett. 57 (1990) 1046
2. Mijatovic D., Eijkel J.C.T., and van den Berg A. Lab. Chip 5 (2005) 492
3. Jegadesan S., Advincula R.C., and Valiyaveettil S. Adv. Mater. 17 (2005) 1282
4. Hayamizu Y., Yamada T., Mizuno K., Davis R.C., Futaba D.N., Yumura M., and Hata K. Nat. Nanotechnol. 3 (2008) 289
5. Zhang S. Nat. Biotechnol. 21 (2003) 1171
6. Ariga K., Nakanishi T., and Hill J.P. Curr. Opin. Colloid Interface Sci. 12 (2007) 106
7. Ariga K., Hill J.P., Lee M.V., Vinu A., Charvet R., and Acharya S. Sci. Technol. Adv. Mater. 9 (2008) 014109
8. Nurmawati M.H., Ajikumar P.K., Renu R., and Valiyaveettil S. Adv. Funct. Mater. 18 (2008) 3213
9. Breen J.M., and Schmitt W. Angew. Chem. Int. Ed. 47 (2008) 6904
10. Sathish M., Miyazawa K., Hill J.P., and Ariga K. J. Am. Chem. Soc. 131 (2009) 6372
11. Rabe J.P., and Buchholz S. Science 253 (1991) 424
12. Yamada N., Ariga K., Naito M., Matsubara K., and Koyama E. J. Am. Chem. Soc. 120 (1998) 12192
13. Shimizu T., Masuda M., and Minamikawa H. Chem. Rev. 105 (2005) 1401
14. Michinobu T., Shinoda S., Nakanishi T., Hill J.P., Fujii K., Player T.N., Tsukube H., and Ariga K. J. Am. Chem. Soc. 128 (2006) 14478
15. Ariga K., Michinobu T., Nakanishi T., and Hill J.P. Curr. Opin. Colloid Interface Sci. 13 (2008) 23
16. Decher G. Science 277 (1997) 1232
17. Ariga K., Hill J.P., and Ji Q. Phys. Chem. Chem. Phys. 9 (2007) 2319
18. Ji Q., Miyahara M., Hill J.P., Acharya S., Vinu A., Yoon S.B., Yu J.-S., Sakamoto K., and Ariga K. J. Am. Chem. Soc. 130 (2008) 2376
19. Ariga K., Vinu A., Ji Q., Ohmori O., Hill J.P., Acharya S., Koike J., and Shiratori S. Angew. Chem. Int. Ed. 47 (2008) 7254
20. Ariga K., Hill J.P., and Ji Q. Macromol. Biosci. 8 (2008) 981
21. Ji Q., Acharya S., Hill J.P., Vinu A., Yoon S.B., Yu J.-S., Sakamoto K., and Ariga K. Adv. Funct. Mater. 19 (2009) 1792
22. Yanagisawa T., Shimizu T., Kuroda K., and Kato C. Bull. Chem. Soc. Jpn. 63 (1990) 988
23. Kresge C.T., Leonowicz M.E., Roth W.J., Vartuli J.C., and Beck J.S. Nature 359 (1992) 710
24. Davis M.E. Nature 417 (2002) 813
25. Lee J., Yoon S., Hyeon T., Oh S.M., and Kim K.B. Chem. Commun. (1999) 2177
26. Ryoo R., Joo S.H., Kruk M., and Jaroniec M. Adv. Mater. 13 (2001) 677
27. Ariga K., Vinu A., Miyahara M., Hill J.P., and Mori T. J. Am. Chem. Soc. 129 (2007) 11022
28. Attard G.S., Göltner C.G., Corker J.M., Henke S., and Templer R.H. Angew. Chem. Int. Ed. 36 (1997) 1315
29. Yamauchi Y., and Kuroda K. Chem. Asian J. 3 (2008) 664
30. Yang P., Zhao D., Margolese D.I., Chmelka B.F., and Stucky G.D. Nature 396 (1998) 152
31. Crepaldi E.L., de G.J., Soler-Illia A.A., Grosso D., Cagnol F., Ribot F., and Sanchez C. J. Am. Chem. Soc. 125 (2003) 9770
32. Vinu A., Ariga K., Mori T., Nakanishi T., Hishita S., Golberg D., and Bando Y. Adv. Mater. 17 (2005) 1648
33. Vinu A., Mori T., and Ariga K. Sci. Technol. Adv. Mater. 7 (2006) 753
34. Stein A., and Schroden R.C. Curr. Opin. Solid State Mater. Sci. 5 (2001) 553
35. Hu X., Li G., Li M., Huang J., Li Y., Gao Y., and Zhang Y. Adv. Funct. Mater. 18 (2008) 575
36. Nishikawa T., Nishida J., Ookura R., Nishimura S., Wada S., Karino T., and Shimomura M. Mater. Sci. Eng. C 8 (1999) 495
37. Nishida J., Nishikawa K., Nishimura S., Wada S., Karino T., Nishikawa T., Ijiro K., and Shimomura M. Polym. J. 34 (2002) 166
38. Park S.H., and Xia Y. Adv. Mater. 10 (1998) 1045
39. Holland B.T., Blanford C.F., Do T., and Stein A. Chem. Mater. 11 (1999) 795
40. Jiang P., Hwang K.S., Mittleman D.M., Bertone J.F., and Colvin V.L. J. Am. Chem. Soc. 121 (1999) 11630
41. Velev O.D., and Kaler E.W. Adv. Mater. 12 (2000) 531
42. Sperschneider A., Schacher F., Gawenda M., Tsarkova L., Müller A.H.E., Ulbricht M., Krausch G., and Köhler J. Small 3 (2007) 1056
43. Watanabe R., Kamata K., and Iyoda T. J. Mater. Chem. 18 (2008) 5482
44. Rayleigh L. Nature 86 (1911) 416
45. Rayleigh L. Nature 90 (1912) 436
46. Karthaus O., Maruyama N., Cieren X., Shimomura M., Hasegawa H., and Hashimoto T. Langmuir 16 (2000) 6071
47. Andreatta A., Tokito S., Smith P., and Heeger A.J. Mol. Cryst. Liq. Cryst. 189 (1990) 169
48. Mattoso L.H.C., MacDiarmid A.G., and Epstein A.J. Synth. Met. 68 (1994) 1
49. Syed A.A., and Dinesan M.K. Analyst 117 (1992) 61
50. Park J.H., Lee C.H., Akagi K., Shirakawa H., and Park Y.W. Synth. Met. 119 (2001) 633
51. Pron A., and Rannou P. Prog. Polym. Sci. 27 (2001) 135
52. Ma X., Li G., Wang M., Bai R., Yang F., and Chen H. Green Chem. 8 (2006) 63
53. Ge C., Armstrong N.R., and Saavedra S.S. Anal. Chem. 79 (2007) 1401
54. Kulkarni M.V., Viswanath A.K., and Khanna P.K. J. Appl. Polym. Sci. 99 (2006) 812
55. Fabre B., and Taillebois L. Chem. Commun. (2003) 2982
56. Hosseini S.H., and Entezami A.A. Polym. Adv. Technol. 12 (2001) 524
57. Pringsheim E., Terpetschnig E., and Wolfbeis O.S. Anal. Chim. Acta 357 (1997) 247
58. Reghu M., Cao Y., Moses D., and Heeger A.J. Phys. Rev. B 47 (1993) 1758
59. Chaudhuri D., Kumar A., Rudra I., and Sarma D.D. Adv. Mater. 13 (2001) 1548
60. Wang H.L., MacDiarmid A.G., Wang Y.Z., Gebler D.D., and Epstein A.J. Synth. Met. 78 (1996) 33
61. Oyama N., Sato M., and Ohsaka T. Synth. Met. 29 (1989) 501
62. Lee J.-W., Park D.-S., Shim Y.-B., and Park S.-M. J. Electrochem. Soc. 139 (1992) 3507
63. Jackowska K., Skompska M., and Przyłuska E. J. Electroanal. Chem. 418 (1996) 35
64. Tagowska M., Pałys B., Mazur M., Skompska M., and Jackowska K. Electrochim. Acta 50 (2005) 2263
65. Palys B.J., Skompska M., and Jackowska K. J. Electroanal. Chem. 433 (1997) 41
66. Nasalska A., and Skompska M. J. Appl. Electrochem. 33 (2003) 113
67. Rutkowska J., Kilian K., and Pyrzynska K. Eur. Polym. J. 44 (2008) 2108
68. Jackowska K., Kudelski A., and Bukowska J. Mater. Sci. Forum. 191 (1995) 247
69. Majid S., El Rhazi M., Amine A., Curulli A., and Palleschi G. Microchim. Acta 143 (2003) 195
70. Li X.-G., Huang M.-R., and Li S.-X. Acta Mater. 52 (2004) 5363
71. Norris I.D., and Mattes B.R. In: Skotheim T.A., and Reynolds J.R. (Eds). Handbook of Conducting Polymers. 3rd ed. vol. 2 (2007), CRC Press LLC, Boca Raton, FL, USA pp. 2/1-2/72
72. Janošević A., Ciric-Marjanović G., Marjanović B., Holler P., Trchova M., and Stejskal J. Nanotechnology 19 (2008) 135606/1-135606/8
73. Ding H., Shen J., Wan M., and Chen Z. Macromol. Chem. Phys. 209 (2008) 864
74. Stejskal J., Sapurina I., Trchová M., and Konyushenko E.N. Macromolecules 41 (2008) 3530
75. Curulli A., Valentini F., Orlanducci S., Terranova M.L., Paoletti C., and Palleschi G. Sens. Actuat. B 100 (2004) 65
76. Stejskal J., Sapurina I., Trchova M., Konyushenko E.N., and Holler P. Polymer 47 (2006) 8253
77. Dimitriev O.P., Ogurtsov N.A., Pud A.A., Smertenko P.S., Piryatinski Y.P., Noskov Y.V., Kutsenko A.S., and Shapoval G.S. J. Phys. Chem. C 112 (2008) 14745
78. Posudievsky O.Y., Biskulova S.A., and Pokhodenko V.D. J. Mater. Chem. 14 (2004) 1419
79. Dexmer J., Leroy C.M., Binet L., Heresanu V., Launois P., Steunou N., Coulon C., Maquet J., Brun N., Livage J., and Backov R. Chem. Mater. 20 (2008) 5541
80. Prakash S., Rao C.R.K., and Vijayan M. Electrochim. Acta 53 (2008) 5704
81. Shim G.H., Han M.G., Sharp-Norton J.C., Creager S.E., and Foulger S.H. J. Mater. Chem. 18 (2008) 594
82. Ćirić-Marjanović G., Dondur V., Milojević M., Mojović M., Mentus S., Radulović A., Vuković Z., and Stejskal J. Langmuir 25 (2009) 3122
83. Oka O., Kiyohara O., and Yoshino K. Jpn. J. Appl. Phys. Part 2 30 (1991) L653
84. Lin H., and Chen S. Macromolecules 33 (2000) 8117
85. Ye S., Do N.T., Dao L.H., and Vijh A.K. Synth. Met. 88 (1997) 65
86. Goncalves D., Waddon A., Karasz F.E., and Akcelrud L. Synth. Met. 74 (1995) 197
87. Liao Y.-H., Angelopoulos M., and Levon K. J. Polym. Sci. A 33 (1995) 2725
88. Dhawan S.K., and Trivedi D.C. J. Appl. Polym. Sci. 58 (1995) 815
89. Conklin J.A., Huang S.-C., Huang S.-M., Wen T., and Kaner R.B. Macromolecules 28 (1995) 6522
90. 2), 6.89, 7.99, 8.74 (Ar-H) ppm.
91. Popp F.D., and Catala A. J. Heterocycl. Chem. 1 (1964) 108
92. Maquestiau A., Berte L., Mayence A., and Vanden Eynde J.-J. Synth. Commun. 21 (1991) 2171
93. Jackowska K., Skompska M., and Przyluska E. J. Electroanal. Chem. 418 (1996) 35
94. Poly(perimidine) described in this work should not be confused with the products of the condensation between tetraamines and the anhydrides of aromatic tetracarboxylic acids. See,. Berlin A.A., Liogon'kii B.I., and Shamraev G.M. Russ. Chem. Rev. 40 (1971) 284
95. Li X.-G., Huang M.-R., Duan W., and Yang Y.-L. Chem. Rev. 102 (2002) 2925
96. Stejskal J., and Gilbert R.G. Pure Appl. Chem. 74 (2002) 857
97. Widawski G., Rawiso M., and Francois B. Nature 369 (1994) 387
98. Jenekhe S.A., and Chen X.L. Science 283 (1999) 372
99. Pitois O., and François B. Eur. Phys. J. B 8 (1999) 225
100. Beysens D., and Knobler C.M. Phys. Rev. Lett. 57 (1986) 1433
101. Beysens D. Atmos. Res. 39 (1995) 215
102. Limaye A.V., Narhe R.D., Dhote A.M., and Ogale S.B. Phys. Rev. Lett. 76 (1996) 3762
103. Maruyama N., Koito T., Nishida J., Sawadaishi T., Cieren X., Ijiro K., Karthaus O., and Shimomura M. Thin Solid Films 327 (1998) 854
104. Yabu H., Tanaka M., Ijiro K., and Shimomura M. Langmuir 19 (2003) 6297
105. Yonezawa T., Onoue S., and Kimizuka N. Adv. Mater. 13 (2001) 140
106. Yabu H., Takebayashi M., Tanaka M., and Shimomura M. Langmuir 21 (2005) 3235
107. Karikari A.S., Williams S.R., Heisey C.L., Rawlett A.M., and Long T.E. Langmuir 22 (2006) 9687
108. Yunus S., Delcorte A., Poleunis C., Bertrand P., Bolognesi A., and Botta C. Adv. Funct. Mater. 17 (2007) 1079
109. Srinivasarao M., Collings D., Philips A., and Patel S. Science 292 (2001) 79
110. de Boer B., Stalmach U., van Hutten P.F., Melzer C., Krasnikov V.V., and Hadziioannou G. Polymer 42 (2001) 9097
111. de Boer B., Stalmach U., Melzer C., and Hadziioannou G. Synth. Met. 121 (2001) 1541
112. Haupt M., Miller S., Sauer R., Thonke K., Mourran A., and Moeller M. J. Appl. Phys. 96 (2004) 3065
113. Nishikawa T., Ookura R., Nishida J., Arai K., Hayashi J., Kurono N., Sawadaishi T., Hara M., and Shimomura M. Langmuir 18 (2002) 5734
114. For other examples see:
115. Ejima H., Iwata T., and Yoshie N. Macromolecules 41 (2008) 9846
116. Park M.S., and Kim J.K. Langmuir 20 (2004) 5347
117. Yabu H., and Shimomura M. Chem. Mater. 17 (2005) 5231
118. Bunz U.H.F. Adv. Mater. 18 (2006) 973
119. Song L., Bly R.K., Wilson J.N., Bakbak S., Park J.O., Srinivasarao M., and Bunz U.H.F. Adv. Mater. 16 (2004) 115