Polyketanils: Preparation of π-Conjugated Polymer Bases from p-dibenzoylbenzene with Various Diamines. Protonation with DL-Camphor-10-sulfonic Acid

Abstract

New luminescent materials - aromatic polyketanils (PKs) containing p-phenylene and biphenylene linkages in the backbone and electron-donating side-group substitutions have been synthesized via melt polycondensation (180°C, 24 h). Their structures were confirmed by elemental and spectral Fourier transform infrared, 13Cand 1H NMR, and ultraviolet-visible (UV-vis) analysis. All the PKs were solution-processable and thermally stable, making them potential candidate materials for applications in microelectronics and aerospace. These ketanil polymers showed high thermal stability and well-defined glass transition temperatures (T _g). The temperature at which the polymers lose 10% of their weight (T ₁₀) ranged from 420 to 520°C. Depending on the polymer structure, PKs showed T _g values in the range of 133 to 244°C. Moreover, the polymers emit either blue radiation or green radiation depending on the mutual presence of conjugated and saturated chain segments. The HOMO/LUMO energy gap of the polymers was in the range of 2.74-2.19 eV. The photoluminescence properties of the PKs after protonation with DL-camphor-10-sulfonic acid (CSA) were tested. The structure formation of (PKs)₁(CSA)₂ complexes are discussed on the basis of 1HNMRspectroscopy.

Keywords

Polyketanils photoluminescence π-conjugation bathochromic shift hypsochromic shift solubility-improving side groups thermal properties

Get full access to this article

View all access options for this article.

References

Topchiev A V , Korshak V V , Popov U A and Rosenstein L D 1963 J. Polym. Sci., Part C 4 1305-1305

Prot T and Mendel B 1966 Polimery-Tworzywa Wielkoczasteczkowe 11 (3) 118-121

D’Alelio G F , Hornback J M , Strazik W F and Dehner T R 1968 J. Macromol. Sci. - Chem. A2, 237-237

Morgan P W , Kwolek S L and Pletcher T C 1987 Macromolecules 20 729-729

Patel M S and Patel S R 1982 J. Polym. Sci.: Polym.Chem. Ed. 20 1985-1985

Banerjee S , Saxena C , Gutch P K and Gupta D C 1996 Eur. Polym. J. 32 661-661

Volpe A A , Kaufman L G and Dondero R G 1970 in Polymers in Space Research Ch L Segal , M Shen and F N Kelley (eds) ( New York: Marcel Dekker, Inc. )

Volpe A A , Kaufman L G and Dondero R G 1969 J. Polym. Sci., Chem. A3 1087-1087

Kaufman L G , Funke P T and Volpe A A 1970 Macromolecules 3 358-358

10.

Yeakel C , Gower K and Mani R S 1993 Macromol. Chem. 194 2779-2779

11.

Sek D 1981 Polymer J. 13 13-13

12.

Higuchi M , Kimoto A , Kanazawa H and Yamamoto K 1999 Org. Lett. 1 1881-1881

13.

Higuchi M , Kimoto A , Shiki S and Yamamoto K 2000 J. Org. Chem. 65 5680-5680

14.

Yamamoto K , Higuchi M , Shiki S , Tsuruta M and Chiba H 2002 Nature 415 509-509

15.

Higuchi M , Shiki S and Yamamoto K 2000 Org. Lett. 2 3079-3079

16.

Higuchi M , Kanazawa H , Tsuruta M and Yamamoto K 2001 Macromolecules 34 8847-8847

17.

Higuchi M , Shiki S , Ariga K and Yamamoto K 2001 J. Am. Chem. Soc. 123 4414-4414

18.

Williams P A , Ellzey K A , Padias A B and Hall H K Jr 1993 Macromolecules 26 5820-5820

19.

Boone H W and Hall H K Jr 1996 Macromolecules 29 5835-5835

20.

Boone H W , Bryce J , Lindgren T , Padias A B and Hall H K Jr 1997 Macromolecules 30 2797-2797

21.

Ding Y , Boone H W , Anderson J D , Padias A B and Hall H K Jr 2001 Macromolecules 34 5457-5457

22.

Dibattista J , Schmidt B M , Padias A B and Hall H K Jr 2002 J. Polym. Sci. Part A. Polym. Chem. 40 43-43

23.

Sek D , Iwan A and Janeczek H 2002 Polymer J. 34 911-911

24.

Sek D , Iwan A , Janeczek H , Rannou P and Proń A 2004 Thin Solid Films 453-454 362-362

25.

Iwan A , Sek D , Kasperczyk J , Mazurak Z , Rannou P and Proń A 2004 New J.Chem. 12 1554-1554

26.

Iwan A , Sek D , Rannou P , Kasperczyk J , Janeczek H , Mazurak Z and Proń A 2004 Synth. Met. 143 331-331

27.

Eastmond G C , Paprotny J and Webster I 1993 Polymer 34 2865-2865

28.

Eastmond G C , Page P C B , Paprotny J , Richards R E and Shaunak R 1994 Polymer 35 4215-4215

29.

Miteva T , Palmer L , Kloppenburg L , Neher D and Bunz U H F 2000 Macromolecules 33 652-652

30.

Walters K A , Ley K D and Schanze K S 1999 Langmuir 15 5676-5676

31.

Oelkrug D , Tompert A , Gierschner J , Egelhaaf H , Hanack M , Hohloch M and Steinhuber E 1989 J. Phys. Chem. 93 5999-5999

32.

Ding L , Karasz F E , Lin Y , Pang Y and Liap L 2003 Macromolecules 36 7301-7301