{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,7]],"date-time":"2026-02-07T22:28:56Z","timestamp":1770503336707,"version":"3.49.0"},"reference-count":50,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2009,11,19]],"date-time":"2009-11-19T00:00:00Z","timestamp":1258588800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Polyimides having dendritic side chains were investigated. The terphenylene diamine monomer having a first-generation monodendron, 3,4,5-tris(n-dodecyloxy)-benzoate and the monomer having a second-generation monodendron, 3,4,5-tris[-3\u2019,4\u2019,5\u2019-tri(n-dodecyloxy)benzyloxy]benzoate were successfully synthesized and the corresponding soluble dendritic polyimides were obtained by polycondensation with conventional tetracarboxylic dianhydride monomers such as benzophenone tertracarboxylic dianhydride (BTDA). The two-step polymerizations in NMP that is a general method for the synthesis of soluble polyimides is difficult; however, the expected dendritic polyimides can be obtained in aromatic polar solvents such as m-cresol and pyridine. The solubility of these dendoronized polyimides is characteristic; soluble in common organic solvents such as dichloromethane, chloroform, toluene and THF. These dendronized polyimides exhibited high glass transition temperatures and good thermal stability in both air and under nitrogen. Their application as alignment layers for LCDs was investigated, and it was found that these polyimides having dendritic side chains were applicable for the vertically aligned nematic liquid crystal displays (VAN-LCDs).<\/jats:p>","DOI":"10.3390\/ijms10115031","type":"journal-article","created":{"date-parts":[[2009,11,19]],"date-time":"2009-11-19T12:39:06Z","timestamp":1258634346000},"page":"5031-5053","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Dendronized Polyimides Bearing Long-Chain Alkyl Groups and Their Application for Vertically Aligned Nematic Liquid Crystal Displays"],"prefix":"10.3390","volume":"10","author":[{"given":"Yusuke","family":"Tsuda","sequence":"first","affiliation":[{"name":"Department of Biochemistry & Applied Chemistry, Kurume National College of Technology, 1-1-1 Komorino, Kurume, Fukuoka 830-8555, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jae Min","family":"OH","sequence":"additional","affiliation":[{"name":"Department of Biochemistry & Applied Chemistry, Kurume National College of Technology, 1-1-1 Komorino, Kurume, Fukuoka 830-8555, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Renpei","family":"Kuwahara","sequence":"additional","affiliation":[{"name":"Department of Biochemistry & Applied Chemistry, Kurume National College of Technology, 1-1-1 Komorino, Kurume, Fukuoka 830-8555, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2009,11,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Mittal, KL (1984). Polyimides; Synthesis, Characterization and Applications, Plenum Press.","DOI":"10.1007\/978-1-4615-7637-2"},{"key":"ref_2","unstructured":"Ghosh, MK, and Mittal, KL (1996). Polyimides; Fundamentals and Applications, Marcel Dekker."},{"key":"ref_3","unstructured":"Mittal, KL (2005). Polyimides and Other High Temperature Polymers, VSP\/Brill."},{"key":"ref_4","unstructured":"Mittal, KL (2007). Polyimides and Other High Temperature Polymers, VSP\/Brill."},{"key":"ref_5","unstructured":"Mittal, KL (2009). Polyimides and Other High Temperature Polymers, VSP\/Brill."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"22","DOI":"10.1002\/pi.2103","article-title":"Synthesis and Characterization of Organo-soluble Fluorinated Polyimides","volume":"56","author":"Hariharan","year":"2007","journal-title":"Polym. Int"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1442","DOI":"10.1002\/app.24616","article-title":"Synthesis and Characterization of Organosoluble Polyfluorinated Polyimides Derived from 3,3,5,5-Tetrafluoro-4,4-diaminodiphenylmethane and Various Aromatic Dianhydrides","volume":"103","author":"Zhao","year":"2007","journal-title":"J. Appl. Polym. Sci"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3082","DOI":"10.1016\/j.polymer.2007.03.065","article-title":"A new class of high Tg and organosoluble polynaphthalimides","volume":"48","author":"Li","year":"2007","journal-title":"Polymer"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2395","DOI":"10.1002\/app.25909","article-title":"Synthesis and Gas Permeability of Novel Fluorinated Poly(phenylene-co-naphthalimide)s","volume":"104","author":"Qiu","year":"2007","journal-title":"J. Appl. Polym. Sci"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1002\/app.27109","article-title":"Formation of Honeycomb Films Based on a Soluble Polyimide Synthesized from 2,2\u2032-Bis[4-(3,4-dicarboxyphenoxy)phenyl] hexafluoropropane dianhydride and 3,3\u2032-Dimethyl-4,4\u2032-diaminodiphenylmethane","volume":"107","author":"Han","year":"2008","journal-title":"J. Appl. Polym. Sci"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2644","DOI":"10.1016\/j.polymer.2008.04.019","article-title":"Soluble Polyimides from Unsymmetrical Diamine Containing Benzimidazole Ring and Trifluoromethyl Pendent Group","volume":"49","author":"Choi","year":"2008","journal-title":"Polymer"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1139","DOI":"10.1016\/j.eurpolymj.2009.01.017","article-title":"Organo-soluble and Transparent Polyimides Containing Phenylphosphine Oxide and Trifluoromethyl Moiety: Synthesis and Characterization","volume":"45","author":"Li","year":"2009","journal-title":"Eur. Polym. J"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1756","DOI":"10.1002\/pola.23269","article-title":"Highly Soluble Fluorinated Polyimides Based on an Asymmetric Bis(ether amine): 1,7-Bis(4-amino-2-trifluoromethylphenoxy)naphthalene","volume":"47","author":"Chung","year":"2009","journal-title":"J. Polym. Sci. A: Polym. Chem"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1016\/j.eurpolymj.2006.09.009","article-title":"Synthesis and Gas Transport Property of Polyimide from 2,2\u2032-Disubstituted biphenyltetracarboxylic dianhydrides (BPDA)","volume":"43","author":"Qiu","year":"2007","journal-title":"Eur. Polym. J"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1163\/156855507782401169","article-title":"New Organo-Soluble Polyimides Based on a New Dianhydride: 4-(4-t-Butyl-phenyl)-2,6-bis(3,4-phenyl dicarboxylic acid anhydride) pyridine","volume":"10","author":"Koohmareh","year":"2007","journal-title":"Des. Monomers Polym"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"3316","DOI":"10.1002\/app.24800","article-title":"Fully Aliphatic Polyimides from Adamantane-Based Diamines for Enhanced Thermal Stability, Solubility, Transparency, and Low Dielectric Constant","volume":"102","author":"Mathews","year":"2006","journal-title":"J. Appl. Polym. Sci"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2250","DOI":"10.1016\/j.polymer.2007.02.061","article-title":"Snthesis and Properties of Novel Soluble Polyimides Having a Spirobisindane-linked Dianhydride Unit","volume":"48","author":"Zhang","year":"2007","journal-title":"Polymer"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1002\/pat.753","article-title":"Highly Soluble Diphenylfluorene-based Cardo Copolyimides Containing Perylene Units","volume":"17","author":"Cao","year":"2006","journal-title":"Polym. Adv. Technol"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1104","DOI":"10.1002\/app.25553","article-title":"Synthesis and Properties of Organosoluble Polynaphthalimides Bearing Ether Linkages and Phthalide Cardo Groups","volume":"104","author":"Yang","year":"2007","journal-title":"J. Appl. Polym. Sci"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1229","DOI":"10.1016\/j.eurpolymj.2005.12.012","article-title":"Synthesis and Characterization of Novel Polyimides Derived from Pyridine-bridged Aromatic Dianhydride and Various Diamines","volume":"42","author":"Wang","year":"2006","journal-title":"Eur. Polym. J"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"212","DOI":"10.1002\/app.25540","article-title":"Synthesis and Characterization of Novel Soluble Pyridine-Containing Polyimides Based on 4-Phenyl-2,6-Bis[4-(4-Aminophenoxy)phenyl]-Pyridine and Various Aromatic Dianhydrides","volume":"104","author":"Wang","year":"2007","journal-title":"J. Appl. Polym. Sci"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4936","DOI":"10.1016\/j.polymer.2006.05.023","article-title":"Soluble Polyimides Containing Trans-diaminotetraphenylporphyrin: Synthesis and Photoinduced Electron Transfer","volume":"47","author":"Anannarukan","year":"2006","journal-title":"Polymer"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2241","DOI":"10.1016\/j.polymer.2007.02.046","article-title":"Synthesis and Optical Properties of Two Series of Soluble Acridine-containing Copolyimides","volume":"48","author":"Xu","year":"2007","journal-title":"Polymer"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2660","DOI":"10.1016\/j.polymer.2006.02.045","article-title":"Synthesis and Properties of Novel Side-chain-sulfonated Polyimides from Bis[4-(4-aminophenoxy)-2-(3-sulfobenzoyl)]phenyl Sulfone","volume":"47","author":"Chen","year":"2006","journal-title":"Polymer"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2862","DOI":"10.1002\/pola.21374","article-title":"Synthesis and Properties of Novel Sulfonated (Co)polyimides Bearing Sulfonated Aromatic Pendant Groups for PEFC Applications","volume":"44","author":"Hu","year":"2006","journal-title":"J. Polym. Sci. A: Polym. Chem"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"6425","DOI":"10.1021\/ma060275k","article-title":"Sulfonated Poly(arylene-co-naphthalimide)s Synthesized by Copolymerization of Primarily Sulfonated Monomer and Fluorinated Naphthalimide Dichlorides as Novel Polymers for Proton Exchange Membranes","volume":"39","author":"Qiu","year":"2006","journal-title":"Macromolecules"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1002\/pola.21778","article-title":"Synthesis and Properties of Novel Sulfonated Polyimides Containing Binaphthyl Groups as Proton-exchange Membranes for Fuel Cells","volume":"45","author":"Li","year":"2007","journal-title":"J. Polym. Sci. A: Polym. Chem"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4911","DOI":"10.1016\/0032-3861(96)81615-6","article-title":"Internal Plasticization of Polyimides with Alkyl 3,5-Diaminobenzoate Compounds","volume":"36","author":"Sasthav","year":"1995","journal-title":"Polymer"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"8894","DOI":"10.1021\/ma960683w","article-title":"Microscopic Molecular Reorientation of Alignment Layer Polymer Surfaces Induced by Rubbing and Its Effects on LC Pretilt Angles","volume":"29","author":"Lee","year":"1996","journal-title":"Macromolecules"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1080\/10587259808044492","article-title":"Effect of Alkyl Side Chain of Soluble Polyimide Orienting Layer on Liquid Crystal Alignment","volume":"316","author":"Lee","year":"1998","journal-title":"Mol. Cryst. Liq. Cryst"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1080\/026782900203290","article-title":"Pretilt Angle for BTDA, PMDA, and CPDA Series Polyimides with Various Side Chain Length","volume":"27","author":"Ban","year":"2000","journal-title":"Liquid Cryst"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/10587259908025991","article-title":"Aromatic Polyimides Containing Pendant Alkyl Groups for Liquid Crystal Alignment Layers","volume":"333","author":"Jung","year":"1999","journal-title":"Mol. Cryst. Liq. Cryst"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1943","DOI":"10.1002\/(SICI)1099-0518(20000601)38:11<1943::AID-POLA30>3.0.CO;2-8","article-title":"Preparation and Properties of High-Pretilt-Angle Polyimides Based on an Alicyclic Dianhydride and Long Alkyloxy Side-group-containing Diamines","volume":"38","author":"Li","year":"2000","journal-title":"J. Polym. Sci., A: Polym. Chem"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"3130","DOI":"10.1002\/pola.20165","article-title":"Synthesis of Novel Polypyromellitimides with n-Alkyloxy Side Chains and Their Liquid-crystal Aligning Property","volume":"42","author":"Lee","year":"2004","journal-title":"J Polym Sci, A: Polym Chem"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"574","DOI":"10.1295\/polymj.29.574","article-title":"Soluble Polyimides Based on 2,3,5-Tricarboxycyclopentyl Acetic Dianhydride","volume":"29","author":"Tsuda","year":"1997","journal-title":"Polym. J"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1295\/polymj.30.222","article-title":"Soluble Copolyimides Based on 2,3,5-Tricarboxycyclopentyl Acetic Dianhydride and Conventional Aromatic Tetracarboxylic Dianhydrides","volume":"30","author":"Tsuda","year":"1998","journal-title":"Polym. J"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1295\/polymj.37.126","article-title":"Soluble Polyimides and Copolyimides Based on Alicyclic Dianhydride Having Cyclohexene and Tetralin Moieties","volume":"37","author":"Tsuda","year":"2005","journal-title":"Polym. J"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"594","DOI":"10.1295\/polymj.32.594","article-title":"Soluble Polyimides Based on Alkyldiaminobenzophenone","volume":"32","author":"Tsuda","year":"2000","journal-title":"Polym J"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"941","DOI":"10.1295\/polymj.32.941","article-title":"Soluble Polyimides Based on Alkyloxydiaminobenzene","volume":"32","author":"Tsuda","year":"2000","journal-title":"Polym. J"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1043","DOI":"10.1295\/polymj.PJ2005257","article-title":"Soluble Polyimides Based on Diaminobenzoic Acid Alkylester","volume":"38","author":"Tsuda","year":"2006","journal-title":"Polymer J"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"354","DOI":"10.1295\/polymj.PJ2007169","article-title":"Soluble Polyimides Based on Long-chain Alkyl Groups via Amide Linkages","volume":"40","author":"Tsuda","year":"2008","journal-title":"Polym. J"},{"key":"ref_42","first-page":"267","article-title":"Polyimides Having Dendron Side Chains","volume":"29","author":"Tsuda","year":"2004","journal-title":"Trans. Mater. Res. Soc. Jpn"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1295\/polymj.38.88","article-title":"Synthesis of Soluble Polyimides Based on Alicyclic Dianhydride in Ionic Liquids","volume":"38","author":"Tsuda","year":"2005","journal-title":"Polym. J"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1539","DOI":"10.1021\/ja963295i","article-title":"Rational Design of the First Spherical Supramolecular Dendrimers Self-Organized in a Novel Thermotropic Cubic Liquid-Crystalline Phase and the Determination of Their Shape by X-ray Analysis","volume":"119","author":"Balagurusamy","year":"1997","journal-title":"J Am Chem Soc"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"4249","DOI":"10.1021\/ja9943400","article-title":"Design and Structural Analysis of the First Spherical Monodendron Self-Organizable in a Cubic Lattice","volume":"122","author":"Percec","year":"2000","journal-title":"J. Am. Chem. Soc"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3133","DOI":"10.1002\/app.1986.070320121","article-title":"High-Strength-High-Modulus Polyimide Fibers I. One-Step Synthesis of Spinnable Polyimides","volume":"32","author":"Kaneda","year":"1986","journal-title":"J. Appl. Polym. Sci"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1002\/(SICI)1097-4628(19960404)60:1<123::AID-APP14>3.0.CO;2-9","article-title":"Comparison of One-Pot and Two-Step Polymerization of Polyimide from BPDA\/ODA","volume":"60","author":"Inoue","year":"1996","journal-title":"J. Appl. Polym. Sci"},{"key":"ref_48","unstructured":"Ghosh, MK, and Mittal, KL (1996). Polyimides; Fundamentals and Applications, Marcel Dekker."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"889","DOI":"10.1021\/ma061763v","article-title":"Synthesis and Properties of Polyimides Containing Multiple Alkyl Side Chains","volume":"40","author":"Wang","year":"2007","journal-title":"Macromolecules"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"132","DOI":"10.1295\/polymj.38.132","article-title":"Organo-Soluble and Lightly-Colored Fluorinated Polyimides Based on 2,2-Bis[4-(3,4-dicarboxyphenoxy)phenyl]hexafluoropropane Dianhydride and Aromatic Bis(ether amine)s Bearing Pendent Trifluoromethyl Groups","volume":"38","author":"Yang","year":"2006","journal-title":"Polym. J"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/10\/11\/5031\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T22:11:43Z","timestamp":1760220703000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/10\/11\/5031"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,11,19]]},"references-count":50,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2009,11]]}},"alternative-id":["ijms10115031"],"URL":"https:\/\/doi.org\/10.3390\/ijms10115031","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,11,19]]}}}