New Soluble Polyimides Containing the Hydroxylic Group. II: Polymers Substituted with Disperse Red 1

Abstract

A series of aromatic polyimides synthesized from various diamidedianhydrides and 2,4-diamino-phenol dihydrochloride were substituted with 4-[N-ethyl-N-(2-hydroxyethyI)Iamino-4'-nitro-azobenzene (Disperse Red 1) via the Mitsunobu reaction. The content of the chromophore in the polyimides has been detenrnined by UV-Vis spectroscopy. The influence of the polyimide structure on the ability for the introduction of the chromophore into the polymers was investigated. Different conditions of the Mitsunobu reaction have enabled the synthesis of polyimides with various contents of DR 1. The induction of optical anisotropy in films of the photochromic polymers was studied by irradiating with the linearly polarized light of an Ar+ laser (488 nm). A dichroism up to 0.2 was induced depending on the content of the push-pull substituted azobenzene side group in these polyimides.

Keywords

Thermostable polymers polyimides poly(o-hydroxyimide)s poly(amideimide)s functionalized polyimides Mitsunobu reaction photo-orientation photo-induced dichroism azobenzene

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References

[1] Sek D , Schab-Balcerzak E and Iwan A 2002 Recent Progress in Polycondensation T. Matsumoto , ed. ( India; Kerala: Research Signpost ) 227-227

[2] Robello D R 1990 J Polym. Sci, Polym. Chem. 28 1-1

[3] Chen T-A , Jen A K-Y and Cai Y 1996 Macromolecules 29 535-535

[4] Shin D Ch , Chang Y , Kim J S , Noh I , Kim Ch and Song K 1999 Polymer Journal 31 1200-1200

[5] Chen T-A , Jen AK-Y and Cai Y 1995 J. Am. Chem. Soc. 117 7295-7295

[6] Lee H-J , Lee M-H , Oh M-Ch and Han S G 1999 Polym. Bull. 42 403-403

[7] Jung Ch , Aoyama T , Wada T , Sasabe H , Jikei M and Kakimoto M 2000 High Perform. Polym. 12 205-205

[8] Ichimura K 1996 Photoregulation of liquid crystal alignment by photochromic molecules and polymeric thin films. In Polymers as Electrooptical and Photooptical Active Media V Shibaev , ed ( Berlin: Springer )

[9] McArdle C B 1989 The application of side chain liquid crystalline polymers in optical data storage. in Side Chain Liquid Crtystalline Polymers CBMcArdle , ed ( Glasgow: Blackie ) 15V-15V

10.

[10] Shibaev P , Kostromin S G and lvanov S A 1996 Comb-shaped polymers with mesogenic side groups as electroand photooptical active media. In Polymers as Electrooptical and Photooptical Active Media, V Shibaev , ed. ( Berlin: Springer )

11.

[11] Xie S , Natansolhn A and Rochon P 1993 Chem. Mater. 5 403-403

12.

[12] Läsker L , Fischer Th , Stumpe J , Kostromin S , Ivanov S , Shibaev V and Ruhmann R 1994 Mol. Cryst. Liq.Cryst. 246 347-347

13.

[13] Fischer Th , Läsker L and Stumpe J 1994 J Photochem Photobiol. A: Chem. 80 453-453

14.

[14] Läsker L , Stumpe J , Fischer Th , Kostromin S , Ivanov S , Shibaev V and Ruhmann R 1994 Mol. Cryst. Liq.Cryst. 253 293-293

15.

[15] Stumpe J , Läsker L , Fischer Th , Kostromin S and Ruhmann R 1996 Thin Solid Films 284 252-252

16.

[16] Fischer Th , Läsker L , Czapla S , Rübner J and Stumpe J 1997 J Mol. Cryst. Liq.Cryst. 297 489-489

17.

[17] Fischer Th , Lasker L , Rutloh M , Czapla S and Stumpe J 1997 J Mol. Cryst. Liq.Cryst. 299 293-293

18.

[18] Stumpe J , Fischer Th , Rutloh M , Rosenhauer R and Meier J G 1999 Proc. SPIE 3800 150-150

19.

[19] Rosenhauer R , Fischer Th , Czapla S , Stumpe J , Viñuales A , Pinol M and Serrano J L 2001 Mol. Cryst. Liq.Cryst. 364 295-295

20.

[20] Rosenhauer R , Fischer Th , Stumpe J , Pinol M and Serrano J L Proc. 2002 SPIE 4000 26-26

21.

[21] Lee H-J , Lee M-H , Han S G , Kim H-Y , Ahn J-H , Lee E-M and Won Y H 1998 J. Polym. Sci. Part A Polym. Chem. 36 301-301

22.

[22] Yang Ch-J and Jenekhe SA 1995 Macromolecules 28 1180-1180

23.

[23] Schab-Balcerzak E and Sęk D 2001 High Perform. Polym. 13 45-45

24.

[24] Bes L , Rousseau A , Boutevin B , Mercier R , Sillion B and Toussaere E 2000 High Perfbrm. Polym. 12 169-169

25.

[25] Li Z , Zhao Y , Zhou J and Shen Y 2000 Eur. Polym. J. 36 2417-2417