Novel Semi‐Fluorinated Poly(ether imide)s Derived From 4‐(p‐Aminophenoxy)‐3‐trifluoromethyl‐4′‐aminobiphenyl

Abstract

An unsymmetrical diamine monomer 4‐(p‐aminophenoxy)‐3‐trifluoromethyl‐4′‐aminobiphenyl has been synthesized successfully. This monomer leads to the synthesis of different novel poly(ether imide)s when reacted with different dianhydrides like pyromellatic dianhydride (PMDA), benzophenone tetracarboxylic acid dianhydride (BTDA), 2,2‐bis(3,4‐dicarboxyphenyl) hexafluoropropane (6FDA), and oxy diphthalic anhydride (ODA). The poly(ether imide) prepared from this monomer on reaction with 6FDA is soluble in several organic solvents such as N‐methylpyrolidinone (NMP), dimethylformamide (DMF), N,N‐dimethylacetamide (DMAc), tetrahydrofuran (THF), and CHCl3. The poly(ether imide)s prepared from BTDA and ODA are soluble in NMP, DMF, and DMAc but not in THF or CHCl3, whereas the polymer prepared from PMDA is soluble only in NMP. The water uptake value for these poly(ether imide) films is very low (0.2–0.5%), and exhibited low dielectric constants (2.81 at 1 MHz). The polymers exhibited high thermal stability up to 532 °C in air for 5% weight loss, and high glass transition temperatures up to 288 °C. The polymer exhibited high tensile strength up to 135 MPa, modulus 3.2 GPa, and elongation at break up to 25%, depending on the exact polymer structure.The structure of the poly(ether imide) synthesised from 4‐(p‐aminophenoxy)‐3‐trifluoromethyl‐4′‐aminobiphenyl and 2,2‐bis(3,4‐dicarboxyphenyl) hexafluoropropane. This polymer was soluble in many organic solvents.magnified imageThe structure of the poly(ether imide) synthesised from 4‐(p‐aminophenoxy)‐3‐trifluoromethyl‐4′‐aminobiphenyl and 2,2‐bis(3,4‐dicarboxyphenyl) hexafluoropropane. This polymer was soluble in many organic solvents.

Polyimides 7: Synthesis, characterization, and properties of novel soluble semifluorinated poly(ether imide)s

“…Kim's findings 29 insisted us to design the unsymmetrical monomer VI. However, the solubility of the poly(-ether imide)s derived from this monomer 30 was not on par with Kim's findings. This provoked us to further manipulate the chemical structures of the diamine monomer through simple chemistry that can result in useful polymer structures having the define set of properties.…”

“…The synthesis of the compound 3-trifluoromethyl-4-fluoro-4 0 -nitro biphenyl was reported in our previous article. 30 Synthesis of diamine monomers VI, VII, and VIII…”

Side chain effects in the packing structure and stiffness of redox-responsive ferrocene-containing polymer brushes

“…All polymers are stable below 210°C, and the value of T g increases with decreasing n from T g = À3.5°C for n = 9 to T g = 148.5°C for n = 1. In general, low T g values suggest the polymer is soft while high T g values indicates rigid polymer structure [60,61]. We also found a reasonably good agreement between E app and T g as T g increases with increasing E app as shown in Fig.…”

Organosoluble, thermally stable and low dielectric constant fluorinated polyimides containing 2,4,5-triphenylimidazole moiety in the main chains

“…Recent studies demonstrated that polyimides derived from ether-bridged aromatic diamines with trifluoromethyl (-CF 3 ) groups are soluble high-temperature polymeric materials with low-moisture uptake, low dielectric constant, high optical transparency and low birefringence. [22][23][24][25][26][27][28][29] Imidazole ring is a useful n-type building block with high-electron affinity and good thermal stability and has been successfully incorporated in small molecules and polymers as the electron-transport component of OLEDs.…”