Triptycene poly(ether-imide)s with high solubility and optical transparency

Hsiao, Sheng‐Huei; Wang, Huimin; Chou, Ji-Shian; Guo, Wenjeng; Lee, Tzong‐Ming; Leu, Chyi‐Ming; Su, Chun-Wei

doi:10.1007/s10965-011-9757-5

Cited by 27 publications

(7 citation statements)

References 57 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In this study, we extend the efforts to develop a new series of entirely iptycene-based polyimides derived from a triptycene-containing dianhydride (TPDAn) , and our previously reported iptycene-containing diamines as well as a −C(CF 3 ) 2 – bridged diamine (i.e., 6FAP, 2,2′-bis(3-amino-4-hydroxyphenyl)hexafluoropropane) that mirrors 6FDA dianhydride structure in comparable polyimides. This new series of triptycene–dianhydride based polyimide membranes are discussed in depth regarding their synthesis (both the monomer and polymers) and characterization with a focus on establishing the correlation between the monomer/polymer structure and free volume architecture in the membranes by comparing them with our previously reported iptycene-containing polyimides.…”

Section: Introductionmentioning

confidence: 88%

Finely Tuning the Free Volume Architecture in Iptycene-Containing Polyimides for Highly Selective and Fast Hydrogen Transport

et al. 2016

View full text Add to dashboard Cite

Iptycene-based polyimides have attracted extensive attention recently in the membrane gas separation field due to their unique structural hierarchy and chemical characteristics that enable construction of well-defined yet tailorable free volume architecture for fast and selective molecular transport. We report here a new series of iptycene-based polyimides that are exquisitely tuned in the monomer structure to afford preferred microcavity architecture for hydrogen transport. In particular, a triptycene-containing dianhydride (TPDAn) was prepared to react with two iptycene-containing diamines (i.e., TPDAm and PPDAm) or 2,2′-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (6FAP) to produce entirely or partially iptycene-based polyimides. The incorporation of iptycene units effectively disrupted chain packing, which resulted in ultrafine microporosity in the membranes with a desired bimodal size distribution with maxima at ∼3 and ∼7 Å, respectively. Depending on the combination of diamine and dianhydride, the microporosity was feasibly tuned and optimized to meet the needs of challenging H2 separations, especially for H2/N2 and H2/CH4 gas pairs. Particularly, a H2 permeability of 27 barrers and H2/N2 and H2/CH4 selectivities of 142 and 300, respectively, were obtained for TPDAn-6FAP.

show abstract

Section: Introductionmentioning

confidence: 88%

Finely Tuning the Free Volume Architecture in Iptycene-Containing Polyimides for Highly Selective and Fast Hydrogen Transport

et al. 2016

View full text Add to dashboard Cite

show abstract

“…6,7 Therefore, the development of highly optical transparent and colorless PI films with high glass transition temperature ( T g ) is an urgent need, which attracts more and more attention of researchers from both academic and commercial perspectives. In the past decades, many attempts have been made to improve the optical properties of PIs based on structural design by three approaches: the incorporation of fluorinated substituents, 8 –15 the attachment of bulky groups, 16 –20 and the introduction of the alicyclic moieties in the polymer chains. 21 –29…”

Section: Introductionmentioning

confidence: 99%

Synthesis of organosoluble and transparent phenolphthalein-based cardo poly(ether sulfone imide)s via aromatic nucleophilic substitution polymerization

Liu

Chen

et al. 2016

High Performance Polymers

View full text Add to dashboard Cite

A series of cardo poly(ether sulfone imide)s (PESI-C) containing bulky phthalide groups were prepared via aromatic nucleophilic substitution reaction of phenolphthalein with 4,4′-difluorodiphenyl sulfone and 4,4′-bis(4-fluorophthalimido)diphenyl ether (BFPI). The glass transition temperatures and 5% weight loss temperatures in nitrogen of the resulting PESI-C increased from 258°C to 278°C and from 468°C to 495°C with increasing the content of imide moiety in the polymer chain, respectively. These PESI-C films were transparent and essentially colorless and exhibited good mechanical properties with tensile strengths of 91–124 MPa, elongations at break of 6.9–12.8%, and tensile moduli of 2.2–2.8 GPa, respectively. It is noted that the tensile strengths, elongations at break, and tensile moduli of PESI-C also increased with increasing the content of BFPI in the copolymerization, indicating that the properties could be adjusted by controlling the ratio of BFPI and 4,4′-difluorodiphenyl sulfone.

show abstract

“…4 It has been generally recognized that arylether linkage imparts properties such as better solubility, melt processing characteristics, and improved toughness in comparison with those polymers without an aryl-ether linkage. [5][6][7][8][9][10] However, the decrease in mechanical properties on heating is almost always a consequence of the reduced chain stiffness or T g s. The introduction of bulky, rigid units in the polymer main chain or as pendent groups can impart an increase in T g s by restricting the segmental mobility, while providing an enhanced solubility because of decreased packing density and crystallinity. 11,12 Thus, combining these two structural modifications minimized the trade-off between the processability and the useful/positive properties of aromatic polyimides.…”

mentioning

confidence: 99%

Synthesis and properties of novel triptycene‐based polyimides

Hsiao

Wang

Chen

et al. 2011

J. Polym. Sci. A Polym. Chem.

Self Cite

View full text Add to dashboard Cite

Two new triptycene‐containing bis(ether amine)s, 1,4‐bis(4‐aminophenoxy)triptycene (4) and 1,4‐bis(4‐amino‐2‐trifluoromethylphenoxy)triptycene (6), were synthesized, respectively, from the nucleophilic chloro‐displacement reactions of p‐chloronitrobenzene and 2‐chloro‐5‐nitrobenzotrifluoride with 1,4‐dihydroxytriptycene in the presence of potassium carbonate, followed by palladium‐catalyzed hydrazine reduction of the dinitro intermediates. The bis(ether amine)s were polymerized with six commercially available aromatic tetracarboxylic dianhydrides to obtain two series of novel triptycene‐based polyimides 8a–f and 9a–f by using a conventional two‐step synthetic method via thermal and chemical imidizations. All the resulting polyimides exhibited high enough molecular weights to permit the casting of flexible and strong films with good mechanical properties. Incorporation of trifluoromethyl groups in the polyimide backbones improves their solubility and decreases their dielectric constants. The fluorinated polyimides 9d and 9f derived from diamine 6 with 4,4′‐oxydiphthalic anhydride and 2,2‐bis(3,4‐dicarboxyphenyl)hexafluoropropane dianhydride (6FDA), respectively, could afford almost colorless thin films. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

show abstract

Triptycene poly(ether-imide)s with high solubility and optical transparency

Cited by 27 publications

References 57 publications

Finely Tuning the Free Volume Architecture in Iptycene-Containing Polyimides for Highly Selective and Fast Hydrogen Transport

Finely Tuning the Free Volume Architecture in Iptycene-Containing Polyimides for Highly Selective and Fast Hydrogen Transport

Synthesis of organosoluble and transparent phenolphthalein-based cardo poly(ether sulfone imide)s via aromatic nucleophilic substitution polymerization

Synthesis and properties of novel triptycene‐based polyimides

Contact Info

Product

Resources

About