{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,3]],"date-time":"2026-09-03T22:37:58Z","timestamp":1788475078661,"version":"build-2803163510"},"reference-count":39,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2020,7,4]],"date-time":"2020-07-04T00:00:00Z","timestamp":1593820800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002850","name":"Fondo Nacional de Desarrollo Cient\u00edfico y Tecnol\u00f3gico","doi-asserted-by":"publisher","award":["3160724"],"award-info":[{"award-number":["3160724"]}],"id":[{"id":"10.13039\/501100002850","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002848","name":"Comisi\u00f3n Nacional de Investigaci\u00f3n Cient\u00edfica y Tecnol\u00f3gica","doi-asserted-by":"publisher","award":["21180253"],"award-info":[{"award-number":["21180253"]}],"id":[{"id":"10.13039\/501100002848","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Fondo de Equipamiento Cient\u00edfico y Tecnol\u00f3gico","award":["EQM120021"],"award-info":[{"award-number":["EQM120021"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Membranes"],"abstract":"<jats:p>A set of five new aromatic poly(imide)s (PIs) incorporating pendant acyclic alkyl moieties were synthesized. The difference among them was the length and bulkiness of the pendant group, which comprises of linear alkyl chains from three to six carbon atoms, and a tert-butyl moiety. The effect of the side group length on the physical, thermal, mechanical, and gas transport properties was analyzed. All PIs exhibited low to moderate molecular weights (Mn ranged between 27.930\u201358.970 Da, and Mw ranged between 41.760\u201381.310 Da), good solubility in aprotic polar solvents, except for PI-t-4, which had a tert-butyl moiety and was soluble even in chloroform. This behaviour was probably due to the most significant bulkiness of the side group that increased the interchain distance, which was corroborated by the X-ray technique (PI-t-4 showed two d-spacing values: 5.1 and 14.3 \u212b). Pure gas permeabilities for several gases were reported (PI-3 (Barrer): He(52); H2(46); O2(5.4); N2(1.2); CH4(1.1); CO2(23); PI-t-4 (Barrer): He(139); H2(136); O2(16.7); N2(3.3); CH4(2.3); CO2(75); PI-5 (Barrer): He(44); H2(42); O2(5.9); N2(1.4); CH4(1.2); CO2(27); PI-6 (Barrer): He(45); H2(43); O2(6.7); N2(1.7); CH4(1.7); CO2(32)). Consistent higher volume in the side group was shown to yield the highest gas permeability. All poly(imide)s exhibited high thermal stability with 10% weight loss degradation temperature between 448\u2013468 \u00b0C and glass transition temperature between 240\u2013270 \u00b0C. The values associated to the tensile strength (45\u201387 MPa), elongation at break (3.2\u201311.98%), and tensile modulus (1.43\u20132.19 GPa) were those expected for aromatic poly(imide)s.<\/jats:p>","DOI":"10.3390\/membranes10070141","type":"journal-article","created":{"date-parts":[[2020,7,6]],"date-time":"2020-07-06T03:19:27Z","timestamp":1594005567000},"page":"141","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["New Poly(imide)s Bearing Alkyl Side-Chains: A Study on the Impact of Size and Shape of Lateral Groups on Thermal, Mechanical, and Gas Transport Properties"],"prefix":"10.3390","volume":"10","author":[{"given":"Fidel E.","family":"Rodr\u00edguez-Gonz\u00e1lez","sequence":"first","affiliation":[{"name":"Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7810000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Germ\u00e1n","family":"P\u00e9rez","sequence":"additional","affiliation":[{"name":"Bureau Veritas Laboratories, 7150 Rue Frederick Banting, Saint-Laurent, Montreal, QC H4S 2A1, Canada"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vladimir","family":"Niebla","sequence":"additional","affiliation":[{"name":"Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7810000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ignacio","family":"Jessop","sequence":"additional","affiliation":[{"name":"Organic and Polymeric Materials Research Laboratory, Departamento de Qu\u00edmica, Universidad de Tarapac\u00e1, Av. General Vel\u00e1squez 1775, P.O. Box 7-D, Arica 1000000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rudy","family":"Martin-Trasanco","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Universidad Tecnol\u00f3gica Metropolitana, J. P. Alessandri 1242, Santiago 7810000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Deysma","family":"Coll","sequence":"additional","affiliation":[{"name":"N\u00facleo de Qu\u00edmica y Bioqu\u00edmica, Facultad de Estudios Interdisciplinarios, Universidad Mayor, Santiago 3830000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pablo","family":"Ortiz","sequence":"additional","affiliation":[{"name":"Centro de Nanotecnolog\u00eda Aplicada, Facultad de Ciencias, Universidad Mayor, Santiago 3830000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manuel","family":"Aguilar-Vega","sequence":"additional","affiliation":[{"name":"Laboratorio de Membranas, Unidad de Materiales, Centro de Investigaci\u00f3n Cient\u00edfica de Yucat\u00e1n A.C. (CICY), Chuburna de Hidalgo, Merida, Yucat\u00e1n 97205, Mexico"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luis H.","family":"Tagle","sequence":"additional","affiliation":[{"name":"Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7810000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudio A.","family":"Terraza","sequence":"additional","affiliation":[{"name":"Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7810000, Chile"},{"name":"UC Energy Research Center, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7810000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8653-8722","authenticated-orcid":false,"given":"Alain","family":"Tundidor-Camba","sequence":"additional","affiliation":[{"name":"Research Laboratory for Organic Polymers (RLOP), Department of Organic Chemistry, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7810000, Chile"},{"name":"UC Energy Research Center, Pontificia Universidad Cat\u00f3lica de Chile, Santiago 7810000, Chile"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,7,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Nunes, S.P., and Peinemann, K.V. (2006). Membrane Technology: In the Chemical Industry, Wiley-VCH.","DOI":"10.1002\/3527608788"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Baker, R.W., and Low, B.T. (2014). Gas separation membrane materials: A perspective. Macromolecules.","DOI":"10.1021\/ma501488s"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"729","DOI":"10.1016\/j.polymer.2013.05.075","article-title":"Energy-efficient polymeric gas separation membranes for a sustainable future: A review","volume":"54","author":"Sanders","year":"2013","journal-title":"Polymer"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"675","DOI":"10.1039\/b600349d","article-title":"Polymers of intrinsic microporosity (PIMs): Organic materials for membrane separations, heterogeneous catalysis and hydrogen storage","volume":"35","author":"McKeown","year":"2006","journal-title":"Chem. Soc. Rev."},{"key":"ref_5","unstructured":"Naiying, D., Jingshe, S., Robertson, G.P., Pinnau, I., and Guiver, M.D. (2008). Linear high molecular weight ladder polymer via fast polycondensation of 5,5\u2032,6,6\u2032-tetrahydroxy-3,3,3\u2032,3\u2032- tetramethylspirobisindane with 1,4-dicyanotetrafluorobenzene. Macromol. Rapid Commun."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.memsci.2009.09.037","article-title":"Thermally rearranged (TR) polymer membranes for CO2 separation","volume":"359","author":"Park","year":"2010","journal-title":"J. Membr. Sci."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1016\/j.nanoen.2018.05.017","article-title":"Stretchable array of high-performance micro-supercapacitors charged with solar cells for wireless powering of an integrated strain sensor","volume":"49","author":"Yun","year":"2018","journal-title":"Nano Energy"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1039\/C8PY00004B","article-title":"Construction of semi-fluorinated polyimides with perfluorocyclobutyl aryl ether-based side chains","volume":"9","author":"Jia","year":"2018","journal-title":"Polym. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Wang, C., Cao, S., Chen, W., Xu, C., Zhao, X., Li, J., and Ren, Q. (2017). Synthesis and properties of fluorinated polyimides with multi-bulky pendant groups. RSC Adv.","DOI":"10.1039\/C7RA01568B"},{"key":"ref_10","unstructured":"Nistor, C., Shishatskiy, S., Popa, M., and Nunes, S.P. (2008). Composite membranes with cross-linked matrimid selective layer for gas separation. Environ. Eng. Manag. J."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Wang, C., Yu, B., Jiang, C., Zhao, X., Li, J., and Ren, Q. (2020). Synthesis and characterization of an aromatic diamine and its polyimides containing asymmetric large side groups. Polym. Bull.","DOI":"10.1007\/s00289-019-03085-3"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Liu, Y., Guo, J., Wang, J., Zhu, X., Qi, D., Li, W., and Shen, K. (2020). A novel family of optically transparent fluorinated hyperbranched polyimides with long linear backbones and bulky substituents. Eur. Polym. J.","DOI":"10.1016\/j.eurpolymj.2020.109526"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Wu, Q., Ma, X., Zheng, F., Lu, X., and Lu, Q. (2019). High performance transparent polyimides by controlling steric hindrance of methyl side groups. Eur. Polym. J.","DOI":"10.1016\/j.eurpolymj.2019.109235"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Tundidor-Camba, A., Terraza, C.A., Tagle, L.H., Coll, D., Ortiz, P., De Abajo, J., and Maya, E.M. (2015). Novel aromatic polyimides derived from 2,8-di(3-aminophenyl)dibenzofuran. Synthesis, characterization and evaluation of properties. RSC Adv.","DOI":"10.1039\/C5RA14456F"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Yi, L., Li, C., Huang, W., and Yan, D. (2015). Soluble polyimides from 4,4\u2032-diaminodiphenyl ether with one or two tert-butyl pedant groups. Polymer.","DOI":"10.1016\/j.polymer.2015.10.045"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Liu, Y., Qian, X., Shi, H., Zhou, W., Cai, Y., Li, W., and Yao, H. (2017). New poly(amide-imide)s with trifluoromethyl and chloride substituents: Synthesis, thermal, dielectric, and optical properties. Eur. Polym. J.","DOI":"10.1016\/j.eurpolymj.2017.07.023"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Yen, H.J., Wu, J.H., Huang, Y.H., Wang, W.C., Lee, K.R., and Liou, G.S. (2014). Novel thermally stable and soluble triarylamine functionalized polyimides for gas separation. Polym. Chem.","DOI":"10.1039\/c4py00449c"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Tundidor-Camba, A., Terraza, C.A., Tagle, L.H., Coll, D., Ortiz, P., P\u00e9rez, G., and Jessop, I.A. (2017). Aromatic polyimides containing cyclopropylamide fragment as pendant group. A study of the balance between solubility and structural rigidity. Macromol. Res.","DOI":"10.1007\/s13233-017-5029-5"},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"P\u00e9rez, G., Terraza, C.A., Coll, D., Ortiz, P., Aguilar-Vega, M., Gonz\u00e1lez, D.M., Tagle, L.H., and Tundidor-Camba, A. (2019). Synthesis and characterization of processable fluorinated aromatic poly(benzamide imide)s derived from cycloalkane substituted diamines, and their application in a computationally driven synthesis methodology. Polymer.","DOI":"10.1016\/j.polymer.2018.12.042"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Murthy, N.S. (2016). X-ray diffraction from polymers. Polymer Morphology: Principles, Characterization, and Processing, Wiley.","DOI":"10.1002\/9781118892756.ch2"},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Bondi, A. (1964). Van der waals volumes and radii. J. Phys. Chem.","DOI":"10.1021\/j100785a001"},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Carrera-Figueiras, C., and Aguilar-Vega, M. (2005). Gas permeability and selectivity of hexafluoroisopropylidene aromatic isophthalic copolyamides. J. Polym. Sci. Part B Polym. Phys.","DOI":"10.1002\/polb.20547"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2385","DOI":"10.1016\/S0032-3861(01)00803-5","article-title":"Hybrid inorganic\u2013organic materials based on a 6FDA\u20136FpDA\u2013DABA polyimide and silica: Physical characterization studies","volume":"43","author":"Cornelius","year":"2002","journal-title":"Polymer"},{"key":"ref_24","unstructured":"Jacobsen, N.E. (2017). NMR Data Interpretation Explained: Understanding 1D and 2D NMR Spectra of Organic Compounds and Natural Products, John Wiley & Sons, Inc.. [1st]."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2294","DOI":"10.1016\/j.polymdegradstab.2007.01.042","article-title":"Chemical modification of copolyimides with bulky pendent groups: Effect of modification on solubility and thermal stability","volume":"92","author":"Maya","year":"2007","journal-title":"Polym. Degrad. Stab."},{"key":"ref_26","unstructured":"Billmeyer, F.W. (1963). Textbook of Polymer Science. Kobunshi."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Privalko, V.P., and Lipatov, Y.S. (1974). Glass Transition and Chain Flexibility of Linear Polymers. J. Macromol. Sci. Part B.","DOI":"10.1080\/00222347408204554"},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Yang, S., He, Y., Liu, Y., and Leng, J. (2019). Shape-memory poly(arylene ether ketone)s with tunable transition temperatures and their composite actuators capable of electric-triggered deformation. J. Mater. Chem. C.","DOI":"10.1039\/C9TC05475H"},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Rivera Nicholls, A., Kull, K., Cerrato, C., Craft, G., Diry, J.B., Renoir, E., Perez, Y., and Harmon, J.P. (2019). Thermomechanical characterization of thermoplastic polyimides containing 4,4\u2019-methylenebis(2,6-dimethylaniline) and polyetherdiamines. Polym. Eng. Sci.","DOI":"10.1002\/pen.24893"},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Hasegawa, M., Horiuchi, M., and Wada, Y. (2007). Polyimides containing trans-1,4-cyclohexane unit (II). Low-K and low-CTE semi- and wholly cycloaliphatic polyimides. High Perform. Polym.","DOI":"10.1177\/0954008306073178"},{"key":"ref_31","doi-asserted-by":"crossref","unstructured":"Cheng, S., Shen, D., Zhu, X., Tian, X., Zhou, D., and Fan, L.J. (2009). Preparation of nonwoven polyimide\/silica hybrid nanofiberous fabrics by combining electrospinning and controlled in situ sol-gel techniques. Eur. Polym. J.","DOI":"10.1016\/j.eurpolymj.2009.06.021"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Hasegawa, M., Fujii, M., Ishii, J., Yamaguchi, S., Takezawa, E., Kagayama, T., and Ishikawa, A. (2014). Colorless polyimides derived from 1S,2S,4R,5R-cyclohexanetetracarboxylic dianhydride, self-orientation behavior during solution casting, and their optoelectronic applications. Polymer.","DOI":"10.1016\/j.polymer.2014.07.032"},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Kim, G., Byun, S., Yang, Y., Kim, S., Kwon, S., and Jung, Y. (2015). Film shrinkage inducing strong chain entanglement in fluorinated polyimide. Polymer.","DOI":"10.1016\/j.polymer.2015.05.038"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Stevens, K.A., Moon, J.D., Borjigin, H., Liu, R., Joseph, R.M., Riffle, J.S., and Freeman, B.D. (2020). Influence of temperature on gas transport properties of tetraaminodiphenylsulfone (TADPS) based polybenzimidazoles. J. Membr. Sci.","DOI":"10.1016\/j.memsci.2019.117427"},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Ogieglo, W., Puspasari, T., Ma, X., and Pinnau, I. (2020). Sub-100 nm carbon molecular sieve membranes from a polymer of intrinsic microporosity precursor: Physical aging and near-equilibrium gas separation properties. J. Membr. Sci.","DOI":"10.1016\/j.memsci.2019.117752"},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Hu, X., He, Y., Wang, Z., and Yan, J. (2018). Intrinsically microporous co-polyimides derived from ortho-substituted Tr\u00f6ger\u2019s Base diamine with a pendant tert-butyl-phenyl group and their gas separation performance. Polymer.","DOI":"10.1016\/j.polymer.2018.08.013"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1016\/j.polymer.2018.01.013","article-title":"Synthesis and properties of new aromatic polyimides containing spirocyclic structures","volume":"137","author":"Terraza","year":"2018","journal-title":"Polymer"},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Robeson, L.M. (1991). Correlation of separation factor versus permeability for polymeric membranes. J. Membr. Sci.","DOI":"10.1016\/0376-7388(91)80060-J"},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Robeson, L.M. (2008). The upper bound revisited. J. Membr. Sci.","DOI":"10.1016\/j.memsci.2008.04.030"}],"container-title":["Membranes"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2077-0375\/10\/7\/141\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T09:47:27Z","timestamp":1760176047000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2077-0375\/10\/7\/141"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,7,4]]},"references-count":39,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2020,7]]}},"alternative-id":["membranes10070141"],"URL":"https:\/\/doi.org\/10.3390\/membranes10070141","relation":{},"ISSN":["2077-0375"],"issn-type":[{"value":"2077-0375","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,7,4]]}}}