Bio-based adenine-containing high performance polyimide
Jianghuai Hu, Zhiping Wang, Zheng Lu, Chang Chen, Meng Shi, Jianbo Wang, Erjin
Zhao, Ke Zeng*, and Gang Yang*
State Key Laboratory of Polymer Materials Engineering, College of Polymer Science
and Engineering, Sichuan University, Chengdu 610065, P. R. China
*Corresponding author: (1) e-mail: [email protected] (Ke Zeng); (2) e-mail:
[email protected] (Gang Yang), Tel: +86-28-85462736, Fax +86-28-
85462736
Electronic supplementary information
Fig. S1 The 1H NMR spectra of p-NBA, p-APA and API.
Fig. S2 The Film of API
Fig. S3 Curve-resolved FT-IR spectra in the range of 3430–3300 cm-1 at different
temperatures of API film (bend 1 belongs to the free N-H stretch, bend 2 belongs to
the bonding N-H stretch, and the peak values of each band are collected in the Figure
2c).
Fig. S4 The normalized temperature-dependent IR spectra of aromatic C=C band (the
peak values at different temperatures are collected in the Figure 2C).
Table S1 Solubility of API film
Solvents m-Cresol NMP DMSO DMF DMAc THF Acetone MC Acetonitrile
Solute
mass(mg)
10.0
Solvent
volume(mL)
0.2 0.5 0.5 0.5 0.5 2.0 2.0 2.0 2.0
Solubility + + + + + - - - -
+: soluble at room temperature; -: insoluble at room temperature. MC: methylene
chloride.
Fig. S5 The simulation stracture of p-APA
NOTE: the molecular simulation was applied to calculate the stracture p-APA. The
calulation was performed with Focite calculation (Fine quality) and subsequently with
DMol 3 calculation (Task: Energy, Quality: Fine, Functional:B3LYP, Basis set: DNP,
Basis file: 3.5) with the Materials Studio 8.0.
Scheme S1 Synthesis of 6FDA-ODA-PI
Note: The 6FDA-ODA-PI and its film was prepared by the same method which
was used in the API. GPC data of 6FDA-ODA-PI: Mn=9,177, Mw=99,336,
PD=10.824. Density: 1.3746 g/cm-3
Fig. S6 the WAXD patterns of 6FDA-ODA-PI film (πstack: 5.56 Å (15.91º),
chpack: 3.92Å (22.67º)).
Table S2 Thermal and mechanical properties of API films
Atomosphere DSC DMA TGA
Tg (°C) Tg (°C) SMa
(GPa)
T5%(°C) T10%(°C) Char yield(%) at
800°C
Air 363 4.1 506 528 0
Nitrogen 350 513 535 56
Table S3 Thermal and mechanical properties of reported 6FDA-congtaining
polyimides
Polyimides DMA TGA Mechanical properties
Tg
(°C)
T5%
(°C
) N2
T5%
(°C)
Air
Char yield(%)
at 800°C
N2
tensile
strength
(MPa)
rupture
elongation
(%)
elastic
modulus
(GPa)
API 363 513 506 56 144 13 5.6
6FDA-ODA-
PIa
298(D
SC)
510 509 38
PI-458 274 520 492 54 98 7.8 3.4
PI-558 272 508 449 54 87 5.9 3.2
PI-658 273 523 511 54 85 8.7 3.1
PI-559 290 523 59 122 8.2 3.2
PI-659 241 507 60 103 5.4 3.1
PI-759 293 471 61 134 4.2 3.1
PI-859 285 484 57 108 6.1 3.1
PI-959 305 489 59 130 4.4 3.6
6FDA-ODA60 286(D
SC)
511
6FDA-PDA61 392 497 6.2 3.8
6FDA-ODA62 319
6FDA-PDA62 375Homo-
polyimide63
273 526 109 21 2.1
1b64 315(D
SC)
530 61 40 5 2.3
Co-PI-165 267 543 103 8 3.6
Co-PI-565 271 553 113 15 4.7
9e66 321 523 117 6.4 2.3
a Obtained by one-step polymerization by our laboratory, see Scheme S1.
Red: The reported value lower than the API film.
Green: The reported value higher than the API film.
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Fig. S7 DSC curves and the corresponding first derivative curves of API and 6FDA-
ODA-PI under nitrogen atmosphere
Fig. S8 TGA curve (a) and its DTG (b) of API and 6FDA-ODA PI under nitrogen and
air atmosphere
Fig. S9 The typical Tensile stress-strain curve of API film at room temperature (The
partial enlarged drawing of Figure 6)