{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,12]],"date-time":"2026-05-12T03:56:18Z","timestamp":1778558178935,"version":"3.51.4"},"reference-count":48,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2019,12,6]],"date-time":"2019-12-06T00:00:00Z","timestamp":1575590400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministry of Education, Taiwan","award":["108L9006"],"award-info":[{"award-number":["108L9006"]}]},{"DOI":"10.13039\/501100004663","name":"Ministry of Science and Technology, Taiwan","doi-asserted-by":"publisher","award":["MOST 108-3017-F-002-002, 108-3116-F-002-008 and 108-2622-8-006-014"],"award-info":[{"award-number":["MOST 108-3017-F-002-002, 108-3116-F-002-008 and 108-2622-8-006-014"]}],"id":[{"id":"10.13039\/501100004663","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Polymers"],"abstract":"<jats:p>A crucial polymer intermediate, 4-[1-(4-hydroxyphenyl)cyclopentyl]-phenol (bisphenol CP), was developed from dicyclopentadiene (DCPD), a key byproduct of the C5 fraction in petrochemicals. On the basis of bisphenol CP, a diamine, 4,4\u2032-((cyclopentane-1,1-diylbis(4,1-phenylene))bis(oxy))-dianiline (cyclopentyl diamine; CPDA) was subsequently obtained through a nucleophilic substitution of bisphenol CP, followed by the hydrogenation process. By using the CPDA diamine, a series of polyimides with cyclopentyl (cardo) units on the backbone were prepared along with a reference polyimide (API-6F) based on 4,4\u2032-(4,4\u2032-(propane-2,2-diyl)bis(4,1-phenylene))bis(oxy)dianiline (BPAA), and 4,4\u2032-(hexafluoroisopropylidene)-diphthalic anhydride (6FDA) for the exploration of structure-properties relationship. Thanks to the presence of cyclopentyl units, this type of cardo polyimides exhibited comparable tensile properties, especially a large elongation (25.4%). It is also worth noting that CPI-6F exhibited better solubility in organic solvents, such as NMP, DMAc, THF, and chloroform, than the other PIs. Gas separation properties were also evaluated for these cardo-type polyimides.<\/jats:p>","DOI":"10.3390\/polym11122029","type":"journal-article","created":{"date-parts":[[2019,12,6]],"date-time":"2019-12-06T10:41:44Z","timestamp":1575628904000},"page":"2029","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis and Properties of Cyclopentyl Cardo-Type Polyimides Based on Dicyclopentadiene"],"prefix":"10.3390","volume":"11","author":[{"given":"Shih-Chieh","family":"Yeh","sequence":"first","affiliation":[{"name":"Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, Taiwan"},{"name":"Advanced Research Center for Green Materials Science and Technology, National Taiwan University, Taipei 106, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jen-Yu","family":"Lee","sequence":"additional","affiliation":[{"name":"Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chung-Ta","family":"Hsieh","sequence":"additional","affiliation":[{"name":"Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ya-Chin","family":"Huang","sequence":"additional","affiliation":[{"name":"Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kuan-Syun","family":"Wang","sequence":"additional","affiliation":[{"name":"Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7564-1457","authenticated-orcid":false,"given":"Chien-Hsin","family":"Wu","sequence":"additional","affiliation":[{"name":"Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, Taiwan"},{"name":"Advanced Research Center for Green Materials Science and Technology, National Taiwan University, Taipei 106, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chien-Chieh","family":"Hu","sequence":"additional","affiliation":[{"name":"Graduate Institute of Applied Science and Technology, National Taiwan University of Science and Technology, Taipei 106, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shu-Chen","family":"Chiang","sequence":"additional","affiliation":[{"name":"Chung Shan Institute of Science and Technology, Taoyuan 325, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0913-4975","authenticated-orcid":false,"given":"Ru-Jong","family":"Jeng","sequence":"additional","affiliation":[{"name":"Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, Taiwan"},{"name":"Advanced Research Center for Green Materials Science and Technology, National Taiwan University, Taipei 106, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,12,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"959","DOI":"10.1021\/acs.macromol.8b02186","article-title":"A Facile Synthetic Route to Ether Diols Derived from 1,1-cyclopentylenylbisphenol for Robust Cardo-Type Polyurethanes","volume":"52","author":"Wu","year":"2019","journal-title":"Macromolecules"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3071","DOI":"10.1039\/C6PY00378H","article-title":"Cross-linked ROMP Polymers Based on Odourless Dicyclopentadiene Derivative","volume":"7","author":"Saha","year":"2016","journal-title":"Polym. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"786","DOI":"10.1021\/ma950852x","article-title":"Polymerization of Dicyclopentadiene: A Tale of Two Mechanisms","volume":"29","author":"Davidson","year":"1996","journal-title":"Macromolecules"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"3360","DOI":"10.1039\/b902345n","article-title":"Latent Olefin Metathesis Catalysts","volume":"38","author":"Monsaert","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1021\/acsmacrolett.6b00227","article-title":"Frontal Ring-Opening Metathesis Polymerization of Exo-Dicyclopentadiene for Low Catalyst Loadings","volume":"5","author":"Robertson","year":"2016","journal-title":"ACS Macro Lett."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"361","DOI":"10.3390\/polym5020361","article-title":"Ring-Opening Polymerization\u2014An Introductory Review","volume":"5","author":"Nuyken","year":"2013","journal-title":"Polymers"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"8623","DOI":"10.1039\/c3cc44683b","article-title":"A facile Avenue to Conductive Polymer Brushes via Cyclopentadiene\u2013Maleimide Diels\u2013Alder Ligation","volume":"49","author":"Yameen","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1039\/B813485E","article-title":"Solvent-free Diels\u2013Alder Reactions of in Situ Generated Cyclopentadiene","volume":"11","author":"Huertas","year":"2009","journal-title":"Green Chem."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Liu, Y.-L., and Chuo, T.-W. (2013). Self-Healing Polymers Based on Thermally Reversible Diels\u2013Alder Chemistry. Polym. Chem., 4.","DOI":"10.1039\/c2py20957h"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"900","DOI":"10.1016\/j.cclet.2016.12.018","article-title":"Synthesis of 5-vinyl-2-norbornene through Diels\u2013Alder Reaction of Cyclopentadiene with 1,3-butadiene in Supercritical Carbon Dioxide","volume":"28","author":"Meng","year":"2017","journal-title":"Chin. Chem. Lett."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"5837","DOI":"10.1021\/ma970930b","article-title":"Low Dielectric Constant Polyimides Derived from Novel 1,6-Bis[4-(4-aminophenoxy)phenyl]diamantane","volume":"31","author":"Chern","year":"1998","journal-title":"Macromolecules"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2815","DOI":"10.1002\/(SICI)1099-0518(19990801)37:15<2815::AID-POLA16>3.0.CO;2-K","article-title":"Synthesis and Characterization of New Cardo Polyimides Prepared from 5,5-Bis[4-(4-aminophenoxy)phenyl]-4, 7-methanohexahydroindane","volume":"37","author":"Liaw","year":"1999","journal-title":"J. Polym. Sci. A Polym. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2787","DOI":"10.1002\/1099-0518(20000801)38:15<2787::AID-POLA190>3.0.CO;2-3","article-title":"Synthesis and Characterization of New Soluble Cardo Polyamide-imides Containing Cyclododecyl Groups","volume":"38","author":"Liaw","year":"2000","journal-title":"J. Polym. Sci. A Polym. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3865","DOI":"10.1016\/S0032-3861(03)00317-3","article-title":"Synthesis and Characterization of New Soluble Cardo Poly(amide\u2013imide)s Derived from 2,2-Bis[4-(4-trimellitimidophenoxy)phenyl]norbornane","volume":"44","author":"Liaw","year":"2003","journal-title":"Polymer"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.jfluchem.2014.04.016","article-title":"Comparative Investigations on the Effects of Pendent Trifluoromethyl Group to the Properties of the Polyimides Containing Diphenyl-Substituted Cyclopentyl Cardo-Structure","volume":"164","author":"Wang","year":"2014","journal-title":"J. Fluor. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5461","DOI":"10.1021\/acs.chemmater.6b01949","article-title":"Microporous Organic Polyimides for CO2 and H2O Capture and Separation from CH4 and N2 Mixtures: Interplay Between Porosity and Chemical Function","volume":"28","author":"Klumpen","year":"2016","journal-title":"Chem. Mater."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"11453","DOI":"10.1039\/C6TA04337B","article-title":"Microporous Polyimides with Functional Groups for the Adsorption of Carbon Dioxide and Organic Vapors","volume":"4","author":"Li","year":"2016","journal-title":"J. Mater. Chem. A"},{"key":"ref_18","first-page":"281616","article-title":"Synthesis of a Polyimide Porous Porphyrin Polymer for Selective CO2 Capture","volume":"2015","author":"Neti","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"13823","DOI":"10.1039\/C7TA02842C","article-title":"Engineering a Hyperbranched Polyimide Membrane for Shape Memory and CO2 Capture","volume":"5","author":"Yang","year":"2017","journal-title":"J. Mater. Chem. A"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1080\/15685551.2018.1472720","article-title":"Synthesis of Soluble Oligsiloxane-End-Capped Hyperbranched Polyazomethine and their Application to CO2\/N2 Separation Membranes","volume":"21","author":"Xu","year":"2018","journal-title":"Des. Monomers Polym."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1039\/C2PY20632C","article-title":"Polyimide Memory: A Pithy Guideline for Future Applications","volume":"4","author":"Kurosawa","year":"2013","journal-title":"Polym. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"907","DOI":"10.1016\/j.progpolymsci.2012.02.005","article-title":"Advanced Polyimide Materials: Syntheses, Physical Properties and Applications","volume":"37","author":"Liaw","year":"2012","journal-title":"Prog. Polym. Sci."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2191","DOI":"10.1039\/c3tc31890g","article-title":"A High-Temperature Resistant Polyimide Gate Inslulator Surface-Modified with a YOx Interlayer for High-Performance, Solution-Processed Li-Doped ZnO Thin-Film Transistors","volume":"2","author":"Yoon","year":"2014","journal-title":"J. Mater. Chem. C"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1777","DOI":"10.1016\/j.orgel.2013.04.002","article-title":"Photo-Patternable Polyimide Gate Insulator with Fluorine Groups for Improving Performance of 2,7-Didecyl[1]benzothieno[3,2-b][1]benzothiopene (C10-BTBT) Thin-Film Transistors","volume":"14","author":"Won","year":"2013","journal-title":"Org. Electron."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"15521","DOI":"10.1039\/C7CP01535F","article-title":"Metal-Oxide Assisted Surface Treatment of Polyimide Gate Insulators for High-Performance Organic Thin-Film Transistors","volume":"19","author":"Kim","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"12","DOI":"10.1016\/j.orgel.2008.09.002","article-title":"Fully Aromatic Polyimide Gate Insulators with Low Temperature Processability for Pentacene Organic Thin-Film Transistors","volume":"10","author":"Ahn","year":"2009","journal-title":"Org. Electron."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"104","DOI":"10.1016\/j.reactfunctpolym.2017.09.002","article-title":"A review of the latest development of polyimide based membranes for CO2 separations","volume":"120","author":"Favvas","year":"2017","journal-title":"React. Funct. Polym."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1016\/j.progpolymsci.2019.01.004","article-title":"Polyimides Containing Aliphatic\/Alicyclic Segments in the Main Chains","volume":"92","author":"Zhuang","year":"2019","journal-title":"Prog. Polym. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"479","DOI":"10.3144\/expresspolymlett.2018.40","article-title":"Synthesis, Characterization and Gas Separation Properties of Novel Polyimides Containing Cardo and Tert-butyl-m-terphenyl Moieties","volume":"12","author":"Bermejo","year":"2018","journal-title":"Express Polym. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"526","DOI":"10.1016\/j.memsci.2017.10.063","article-title":"Cardo-Type Random Co-Polyimide Membranes for High Pressure Pure and Mixed Sour Gas Feed Separations","volume":"550","author":"Yahaya","year":"2018","journal-title":"J. Membr. Sci."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"13309","DOI":"10.1039\/C4TA02303J","article-title":"Synthesis and Characterization of Triptycene-based Polyimides with Tunable High Fractional Free volume for Gas Separation Membranes","volume":"2","author":"Wiegand","year":"2014","journal-title":"J. Mater. Chem. A"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/S0376-7388(96)00061-0","article-title":"Correlation and Prediction of Gas Permeability in Glassy Polymer Membrane Materials via a Modified Free Volume Based Group Contribution Method","volume":"125","author":"Park","year":"1997","journal-title":"J. Membr. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"578","DOI":"10.1295\/polymj.35.578","article-title":"Optical Properties of Polyimide Thin Films. Effect of Chemical Structure and Morphology","volume":"35","author":"Lee","year":"2003","journal-title":"Polym. J."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"441","DOI":"10.1021\/j100785a001","article-title":"van der Waals Volumes and Radii","volume":"68","author":"Bondi","year":"1964","journal-title":"J. Phys. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1722","DOI":"10.1021\/jo00210a029","article-title":"Selective Indirect Oxidation of Phenol to Hydroquinone and Catechol","volume":"50","author":"Dai","year":"1985","journal-title":"J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Zhang, P., Chen, H., Zhang, L., Ran, T., and Zhang, D. (2016, January 17\u201320). Breath Figure Patterns Prepared by Spraying Ultrasonic Atomized Water Droplets. Proceedings of the 2016 IEEE 11th Annual International Conference on Nano\/Micro Engineered and Molecular Systems (NEMS), Sendai, Japan.","DOI":"10.1109\/NEMS.2016.7758275"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"9491","DOI":"10.1021\/la401991n","article-title":"Bioinspired Design of Honeycomb Structure Interfaces with Controllable Water Adhesion","volume":"29","author":"Heng","year":"2013","journal-title":"Langmuir"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"945","DOI":"10.1002\/app.11393","article-title":"Synthesis and Properties of Polyimides Cotaining Bisphenol Unit and Flexible Ether Linkage","volume":"87","author":"Leu","year":"2003","journal-title":"J. Appl. Polym. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"7529","DOI":"10.1016\/j.polymer.2004.08.062","article-title":"Synthesis and Properties of Organosoluble Polyimides Based on 1,1-bis[4-(4-amino-2-trifluoromethylphenoxy)phenyl]cyclohexane","volume":"45","author":"Yang","year":"2004","journal-title":"Polymer"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"659","DOI":"10.1021\/ma402178z","article-title":"Impact of Backbone Rigidity on the Photomechanical Response of Glassy, Azobenzene-Functionalized Polyimides","volume":"47","author":"Wang","year":"2014","journal-title":"Macromolecules"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.memsci.2015.10.045","article-title":"Liberation of Small Molecules in Polyimide Membrane Formation: An Effect on Gas Separation Properties","volume":"499","author":"Wu","year":"2016","journal-title":"J. Membr. Sci."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"12807","DOI":"10.1039\/C7TC04220E","article-title":"Intrinsic Low Dielectric Constant Polyimides: Relationship Between Molecular Structure and Dielectric Properties","volume":"5","author":"Bei","year":"2017","journal-title":"J. Mater. Chem. C"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1016\/S0376-7388(00)80626-2","article-title":"Isomeric Polyimides Based on Fluorinated Dianhydrides and Diamines for Gas Separation Applications","volume":"50","author":"Coleman","year":"1990","journal-title":"J. Membr. Sci."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"13914","DOI":"10.1039\/c3ta13308g","article-title":"Highly Permeable Chemically Modified PIM-1\/Matrimid Membranes for Green Hydrogen Purification","volume":"1","author":"Yong","year":"2013","journal-title":"J. Mater. Chem. A"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"941","DOI":"10.1016\/j.memsci.2016.08.045","article-title":"Crosslinked MOF-polymer to Enhance Gas Separation of Mixed Matrix Membranes","volume":"520","author":"Nguyen","year":"2016","journal-title":"J. Membr. Sci."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.seppur.2011.06.037","article-title":"MOF-containing Mixed-matrix Membranes for CO2\/CH4 and CO2\/N2 Binary Gas Mixture Separations","volume":"81","author":"Basu","year":"2011","journal-title":"Sep. Purif. Technol."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Scholes, C.A., and Kanehashi, S. (2019). Polymer of Intrinsic Microporosity (PIM-1) Membranes Treated with Supercritical CO2. Membranes, 9.","DOI":"10.3390\/membranes9030041"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1016\/j.memsci.2007.01.034","article-title":"On the Limits of Gas Separation in CO2\/CH4, N2\/CH4 and CO2\/N2 Binary Mixtures Using Polyimide Membranes","volume":"293","author":"Cecopierigomez","year":"2007","journal-title":"J. Membr. Sci."}],"container-title":["Polymers"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4360\/11\/12\/2029\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T13:40:09Z","timestamp":1760190009000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4360\/11\/12\/2029"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,12,6]]},"references-count":48,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2019,12]]}},"alternative-id":["polym11122029"],"URL":"https:\/\/doi.org\/10.3390\/polym11122029","relation":{},"ISSN":["2073-4360"],"issn-type":[{"value":"2073-4360","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,12,6]]}}}