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Two kinds of novel poly(arylene ether nitrile)s (CPDP-DCBN and CHDP-DCBN) containing pendant aliphtatic ring were synthesized by 4,4′-cyclopentane-1,1′-diyldiphenol (CPDP) or 4,4′-cyclohexane-1,1′-diyldiphenol (CHDP) and 2,6-dichlorobenzonitrile (DCBN) in this work. The inherent viscosities of poly(arylene ether nitrile)s (PENs) were in the range of 0.701–0.806 dL g−1. The polymers showed high glass transition temperatures ( T g) of 185.4–196.4°C and weight-loss temperatures ( T5%) of 447.8–454.3°C. The obtained CPDP-DCBN and CHDP-DCBN could be hot pressed into the films, which showed the tensile strengths of 82.6 MPa and 86.8 MPa, respectively. And the storage modulus of CPDP-DCBN and CHDP-DCBN were about 1.0 GPa and 1.5 GPa at 150°C, respectively. Additionally, the PENs could be dissolved in many solutions at room temperature, such as NMP and concentrated H2SO4, indicating that they had good solubility; they can be processed by the solution method. Meanwhile, the optical transmittance of CPDP-DCBN was 78.1% at 450 nm; it has potential to be applied to the heat-resistant optical film.

A series of modified poly(ether ether ketone)s containing different content of benzene pendant group in the molecular chain have been successfully synthesized with 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bisphenol A and 4,4′-difluorobenzophenone by nucleophilic substitution. The inherent viscosities of obtained polymers were in the range of 0.261–0.889 dLg−1. They were found to have high glass transition temperatures (Tg) of 150–168°C and 148–169°C (examined by DSC and DMA, respectively), good thermal stability with 5% weight-loss temperature (T5%) of 439–469°C. The tensile strengths of the obtained polymers were 67.7–86.6 MPa, and the storage modulus was over 0.9 GPa at about 140°C. The modified poly(ether ether ketone)s showed the excellent solubility property, they could be processed by solution method. Additionally, the obtained polymers had good optical transmittance (>70%) at 400 nm, suggesting that they have potential to be applied to the heat-resistant optical films.