4676 Liaw et al.
Macromolecules, Vol. 35, No. 12, 2002
that polyamide (Figure 2, curve A) is more reversible
than polyimide (Figure 2, curve B) and poly(amide-
imide) (Figure 2, curve C) due to the large ability of
electron donating of polyamide than polyimide and poly-
(amide-imide).32 The difference of the oxidation poten-
tial between polyamides and polyimides is due to the
fact that the oxidized triarylamine unit has an electro-
chemical effect on the adjacent units.23 It was observed
that the intensity of redox peaks decreased as cycle time
increased, which can be explained by the dissolution of
ionized polymer into the solvent. The polymer displayed
an electrochromic property, as they were transformed
from the orange neutral form to the blue oxidized form.
1773, 1714, 1379 cm-1 .1H NMR (DMSO-d6): δ (ppm)
) 8.36 (d, 2H), 8.24 (s, 2H), 8.01 (d, 2H), 7.37 (d, 4H),
7.16-7.10 (m, 5H), 7.00 (s, 1H), 6.90 (s, 1H), 2.19 (d,
6H). 13C NMR (DMSO-d6): δ (ppm) ) 168.1, 168.0,
167.5, 148.3, 145.5, 139.4, 137.7, 136.8, 136.1, 134.3,
133.2, 132.2, 129.4, 128.3, 126.8, 124.9, 124.8, 124.5,
123.7, 19.3, 16.7.
Refer en ces a n d Notes
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Con clu sion s
This study successfully prepared the new diamine
DADT and diimide-dicarboxylic acid TDT containing
a triphenylamine group. The polyamides and polyimides
were prepared from DADT with various dicarboxylic
acid and dianhydride, respectively, with moderate to
high inherent viscosity. The diimide-dicarboxylic acid
TDT reacted with various diamines, yielding various
new poly(amide-imide)s. Most of the polyamides, poly-
imides, and poly(amide-imide)s exhibited good solubil-
ity, high glass transition temperature, thermal decom-
position temperature, and tensile properties. Results
presented herein also demonstrated that incorporating
bulky dimethylphenyl group into polymer backbone
enhanced the processability of the rigid polymer back-
bone while maintaining good thermal stability. Thus,
the present polyamides, polyimides, and poly(amide-
imide)s are considered as new promising processable
high-temperature polymeric materials. The investiga-
tion of electrochemical properties suggests that most of
these new polymers have a potential as the type of hole-
transporting materials.
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Ap p en d ix
(A) 4,4′-Din it r o-3′′,4′′-d im et h ylt r ip h en yla m in e
(DNDT). IR spectrum: 1571 and 1334 cm-1 (NO2). H
1
NMR (DMSO-d6, ppm): δ 8.17 (d, 4H), 7.27 (d, 1H), 7.18
(d, 4H), 7.06 (s, 1H), 6.99 (d, 1H), 2.25 (s, 3H), 2.20 (s,
3H). 13C NMR (DMSO-d6, ppm): δ 152.9, 143.1, 142.9,
140.1, 136.9, 132.5, 129.4, 126.5, 125.9, 122.9, 19.1, 18.7.
(B) 4,4′-Dia m in o-3′′,4′′-d im eth yltr ip h en yla m in e
(DADT). IR spectrum: 3412, 3340, and 1601 cm-1 (N-
1
H). H NMR (DMSO-d6, ppm): δ 6.83 (d, 1H), 6.74 (d,
4H), 6.52 (d, 5H), 6.43 (d, 1H), 4.86 (s, 4H), 2.07 (s, 3H),
2.03 (s, 3H). 13C NMR (DMSO-d6, ppm): δ 149.1, 146.3,
138.4, 137.5, 131.0, 127.9, 127.3, 120.9, 117.1, 115.9,
19.7, 18.4.
(31) Ogino, K.; Kanegae, A.; Yamaguchi, R.; Sato, H.; Kurjata, J .
Macromol. Rapid Commun. 1999, 20, 103.
(32) Shirota, Y. J . Mater. Chem. 2000, 10, 1.
(33) Matsumoto, T.; Kurosaki, T. Macromolecules 1997, 30, 993.
(34) Trofimenko, S.; Auman, B. C. Macromolecules 1994, 27, 1136.
(C) 4,4′-Tr im ellitim id o-3′′,4′′-d im eth yltr ip h en y-
la m in e (TDT). IR spectrum: 2500-3475 (C(O)O-H),
MA001523U