Modified Triphenylmethane-based Polyimides with Improved Optical, Dielectric and Solubility Properties <italic style="font-style: italic">via</italic> Post-Polymerization Modification

Yan-Cheng Wu; Guo-Tao Huang; Man-Yu Lian; Rui Liang; Hong-Lin Deng; Feng Gan; Yang-Fan Zhang; Ning-Bo Yi; Li-Yong Tian; Chun-Ping Ma; Yen Wei

doi:10.1007/s10118-023-3018-z

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Modified Triphenylmethane-based Polyimides with Improved Optical, Dielectric and Solubility Properties via Post-Polymerization Modification

RESEARCH ARTICLE | Updated：2023-09-21

- Modified Triphenylmethane-based Polyimides with Improved Optical, Dielectric and Solubility Properties via Post-Polymerization Modification
  Enhanced Publication
- Chinese Journal of Polymer Science Vol. 41, Issue 10, Pages: 1609-1616(2023)
- Affiliations：
  
  a.School of Textile Materials and Engineering, Wuyi University, Jiangmen 529020, China
  b.Department of Chemistry and the Tsinghua Center for Frontier Polymer Research, Tsinghua University, Beijing 100084, China
- Author bio：
  
  wyc@wyu.edu.cn (Y.C.W.)
  machunpingaa@126.com (C.P.M.)
  weiyen@mail.tsinghua.edu.cn (Y.W.)
- Funds：
- DOI：10.1007/s10118-023-3018-z
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Yan-Cheng Wu, Guo-Tao Huang, Man-Yu Lian, et al. Modified Triphenylmethane-based Polyimides with Improved Optical, Dielectric and Solubility Properties via Post-Polymerization Modification. [J]. Chinese Journal of Polymer Science 41(10):1609-1616(2023)
DOI：

Yan-Cheng Wu, Guo-Tao Huang, Man-Yu Lian, et al. Modified Triphenylmethane-based Polyimides with Improved Optical, Dielectric and Solubility Properties via Post-Polymerization Modification. [J]. Chinese Journal of Polymer Science 41(10):1609-1616(2023) DOI： 10.1007/s10118-023-3018-z.

摘要

A post-polymerization modification is developed to prepare a new family of bulky tert-butyldimethylsiloxy modified polyimide films with significantly improved optical, dielectric and solubility properties.

Abstract

A family of new triphenylmethane (TPM)-based polyimides (PIs) containing bulky ,tert,-butyldimethylsiloxy (TBS) side-groups (PI-TPMOSis) has been prepared by a post-polymerization modification ,via, a simple silyl ether reaction of TPM-based PIs containing hydroxyl (OH) groups (PI-TPMOHs). The attachment of TBS side-groups in PI-TPMOSis can be achieved up to 100%, as confirmed by the ,1,H-NMR and IR spectra. Due to the presence of the TPM structure, PI-TPMOSi films still display the excellent thermal stability with high glass transition temperature (,T,g,) of 314−351 °C and high degradation temperature (,T,d5%,) of 480−501 °C. It is quite remarkable that the introduction of TBS side-groups into PI-TPMOSi chains results in more superior optical, dielectric and solubility properties in comparison with the precursor PI-TPMOH films, probably due to the reductions of the packing density and charge-transfer complexes (CTCs) formation. The optical transmittance at 400 nm (,T,400,) of PI-TPMOSi films is significantly increased from 45.3%−68.8% to 75.4%−81.6% of the precursor PI-TPMOH films. The dielectric constant (,D,k,) and dissipation factor (,D,f,) at 1 MHz of PI-TPMOSi films are reduced from 4.11−4.40 and 0.00159−0.00235 to 2.61−2.92 and 0.00125−0.00171 of the precursor PI-TPMOH films, respectively. Combining the molecular design and simple preparation method, this study provides an effective approach for enhancement of various properties of PI films for microelectronic and photoelectric engineering applications.

关键词

Keywords

Triphenylmethane-based polyimidesPost-polymerization modificationHigh TgHigh optical transparenceLow Dk

references

Wang,Y.;Zhou,X.;Feng,X.;Yu,X.;Li,S.;Zhao,J.;Fan,Z.;Sun,X.;Zhang,P.;Cui,J.;Guo,M.;Cheng,B.Polyimidefilmscontainingtrifluoromethoxygroupswithhighcomprehensiveperformanceforflexiblecircuitrysubstrates.ACS Appl. Polym. Mater.2022,4,5831−5839..

Dai,X.;Bao,F.;Jiao,L.;Yao,H.;Ji,X.;Qiu,X.;MenY.High-performancepolyimidecopolymerfibersderivedfrom5-anino-2-(2-hydroxy-4-aminobenzene)-benzoxazole:preparation,structureandproperties.Polymer2018,150,254−266..

Li,J.;Lin,J.;Wang,Y.;Chu,W.;Liu,F.;Wang,B.Cross-linkedandrigidpolyimidecompositefoamswithprominentfireresistant,thermalinsulating,andwave-transparentproperties.ACS Appl. Polym. Mater.2022,4,6994−7003..

Hasegawa,M.;Horie,K.Photophysics,photochemistry,andopticalpropertiesofpolyimides.Prog. Polym. Sci.2001,26,259−335..

Ji,D.;Li,T.;Hu,W.;Fuchs,H.Recentprogressinaromaticpolyimidedielectricsfororganicelectronicdevicesandcircuits.Adv. Mater.2019,1806070..

Li,Y.;Sun,G.;Zhou,Y.;Liu,G.;Wang,J.;Han,S.Progressinlowdielectricpolyimidefilm—areview.Prog. Org. Coat.2022,172,107103..

Yi,C.;Li,W.;Shi,S.;He,K.;Ma,P.;Chen,M.;Yang,C.High-temperature-resistantandcolorlesspolyimide:preparations,properties,andapplications.Sol. Energy2020,195,340−354..

Favvas,E.P.;Katsaros,F.K.;Papageorgiou,S.K.;Sapalidis,A.A.;Mitropoulos,A.C.AreviewofthelatestdevelopmentofpolyimidebasedmembranesforCO2separations.React. Funct. Polym.2017,120,104−130..

Sanaeepur,H.;Amooghin,A.E.Bandehali,S.;Moghadassi,A.;Matsuura,T.;Bruggen,B.V.Polyimidesinmembranegasseparation:monomer’smoleculardesignandstructuralengineering.Prog. Polym. Sci.2019,91,80−125..

Ding,Y.;Hou,H.;Zhao,Y.;Zhu,Z.;Fong,H.Electrospunpolyimidenanofifibersandtheirapplications.Prog. Polym. Sci.2016,61,67−103..

Wu,Y.;Shi,C.;Chen,Z.;Zhou,Y.;Liu,S.;Zhao,J.Anovelhydroxyl-containingpolyimideasacolorimetricandratiometricchemosensorforthereversibledetectionoffluorideions.Polym. Chem.2019,10,1399−1406..

Liu,Y.;Zhou,Z.;Qu,L.;Zou,B.;Chen,Z.;Zhang,Y.;Liu,S.;Chi,Z.;Chen,X.;Xu,J.Exceptionallythermostableandsolublearomaticpolyimideswithspecialcharacteristics:intrinsicultralowdielectricconstant,staticrandomaccessmemorybehaviors,transparencyandfluorescence.Mater. Chem. Front.2017,1,326−337..

Xiao,P.;He,X.;Zheng.F.;Lu,Q.Super-heatresistant,transparentandlowdielectricpolyimidesbasedonspirocyclicbisbenzoxazolediamineswithTg>450°C.Polym. Chem.2022,13,3660−3669..

Zhang,M.;Miao,J.;Xu,Y.;Wang,Z.;Yan,J.Colorlesspolyimidesfromfluorinatedladderdiaminescontainingnorbornylbenzocyclobutenesegments.Macromolecules2022,55,7992−8001..

Chen,G.;Xu,G.;Jiao,Y.;Tang,Y.;Tan,L.;Fang,X.CardopolyimideswithhighTgandtransparencyderivedfrombisphenolfluorenesand1,4-bis(4-fluorophtha-limide)cyclohexanesviaaromaticnucleophilicsubstitution.Eur. Polym. J.2023,188,111911..

Zhong,K.C.;Chen,J.C.;Lee,S.W.;Wu,H.C.Alicyclicdianhydridesandpolyimidescontainingdouble-bondbridgedcyclohexanesandinvestigationsontheirretroDiels-Alderreaction.ACS Appl. Polym. Mater.2023,5,602−613..

Lu,J.;Zhang,Y.;Li,J.;Fu,M.;Zou,G.;Ando,S.;Zhuang,Y.Tröger’sbase(TB)-basedpolyimidesaspromisingheat-insulatingandlow-kdielectricmaterials.Macromolecules2023,56,2164−2174..

Liu,Y.W.;Tang,L.S.;Qu,L.J.;Liu,S.W.;Chi,Z.G.;Zhang,Y.;Xu,J.R.Synthesisandpropertiesofhighperformancefunctionalpolyimidescontainingrigidnonplanarconjugatedfluorenemoieties.Chinese J. Polym. Sci.2019,37,416−427..

Tapaswi,P.K.;Ha,C.S.Recenttrendsontransparentcolorlesspolyimideswithbalancedthermalandopticalproperties:designandsynthesis.Macromol. Chem. Phys.2019,220,1800313..

Zhuang,Y.;Seong,J.G.;LeeY.M.Polyimidescontainingaliphatic/alicyclicsegmentsinthemainchains.Prog. Polym. Sci.2019,92,35−88..

Zuo,H.T.;Gan,F.;Dong,J.;Zhang,P.;Zhao,X.;Zhang,Q.H.Highlytransparentandcolorlesspolyimidefilmwithlowdielectricconstantbyintroducingmeta-substitutedstructureandtrifluoromethylgroups.Chinese J. Polym. Sci.2021,39,455−464..

Lian,R.;Lei,X.;Xiao,Y.;Xue,S.;Xiong,G.;Zhang,Z.;Yana,D.;Zhang,Q.Synthesisandpropertiesofcolorlesscopolyimidesderivedfrom4,4’-diaminodiphenylether-baseddiamineswithdifferentsubstituents.Polym. Chem.2021,12,4803−4811..

Fang,Y.;He,X.;Kang,J.C.;Wang,L.;Ding,T.M.;Lu,X.;Zhang,S.Y.;Lu,Q.Terphenyl-basedcolorlessandheat-resistantpolyimideswithacontrolledmolecularstructureusingmethylsidegroups.Polym. Chem.2022,13,5105−5115..

Li,D.;Wang,C.;Yan,X.;Ma,S.;Lu,R.;Qian,G.;Zhou,H.Heat-resistantcolorlesspolyimidesfrombenzimidazolediamines:Synthesisandproperties.Polymer2022,254,125078..

Constantin,C.P.;Sava,I.;Damaceanu,M.D.Structuralchemistry-assistedstrategytowardfastcis-transphoto/thermalisomerizationswitchofnovelazo-naphthalene-basedpolyimides.Macromolecules2021,54,1517−1538..

Wu,Y.;Liu,S.;Zhao,J.Simultaneouslyimprovingtheoptical,dielectric,andsolubilitypropertiesoffluorene-basedpolyimidewithsilylethersidegroups.ACS Omega2022,7,11939−11945..

Orlova,A.M.;Alentiev,A.Yu.;Kolesnikov,T.I.;Tsegelskaya,A.Y.;Monakhova,K.Z.;Chirkov,S.V.;Nikiforov,R.Y.;Abramov,I.G.;Kuznetsov,A.A.Novelorgano-solublepoly(etherimide)sbasedondiethyltoluenediamine:Synthesis,characterizationandgastransportproperties.Polymer2022,256,125258..

Zhao,X.;Liu,J.;Yang,H.;Fan,L.;Yang,S.Novelpolyfluorinatedpolyimidesderivedfromα,α-bis(4-amino-3,5-difluoro-phenyl)phenylmethaneandaromaticdianhydrides:synthesisandcharacterization.Eur. Polym. J.2008,44,808−820..

Wang,C.Y.;Li,G.;Zhao,X.Y.;Jiang,J.M.Highsolubility,low-dielectricconstant,andopticaltransparencyofnovelpolyimidesderivedfrom3,3',5,5'-tetramethyl-4,4'-diaminodiphenyl-4''-isopropyltoluene.J. Polym. Sci., Part A: Polym. Chem.2009,47,3309−3317..

Zhao,X.J.;Liu,J.G.;Li,H.S.;Fan,L.;Yang,S.Y.Synthesisandpropertiesoffluorinatedpolyimidesfrom1,1-bis(4-amino-3,5-dimethylphenyl)-1-(3,4,5-trifluorophenyl)-2,2,2-trifluoroethaneandvariousaromaticdianhydrides.J. Appl. Polym. Sci.2009,111,2210−2219..

Wang,C.;Zhao,X.;Li,G.;Jiang,J.Highopticaltransparencyandlowdielectricconstantofnovelsolublepolyimidescontainingfluorineandtrifluoromethylgroups.Colloid. Polym. Sci.2011,289,1617−1624..

Sava,I.;Damaceanu,M.D.;Constantin,C.P.;Asandulesa,M.;Wolińska-Grabczyk,A.;Jankowski,A.Structure-promotedhighperformancepropertiesoftriphenylmethane-containingpolyimidesandcopolyimides.Eur. Polym. J.2018,108,554−569..

Cheng,K.;Hu,J.;Wu,Y.;Shi,C.;Chen,Z.;Liu,S.;Yuan,Y.;Mo,Y.;Zhao,J.Microwave-assistedsynthesisofhighthermalstabilityandcolourlesspolyimidescontainingpyridine.R. Soc. Open Sci.2019,6,190196..

Liu,H.;Zhai,L.;Bai,L.;He,M.;Wang,C.;Mo,S.;Fan,L.Synthesisandcharacterizationofopticallytransparentsemi-aromaticpolyimidefilmswithlowfluorinecontent.Polymer2019,163,106−114..

Yuan,C.;Sun,Z.;Wang,Y.Studyontheeffectofdifferentamountsofhydroxylandtert-butylsubstitutedtriphenylpyridineunitsonthepropertiesofpolyimide.J. Polym. Res.2020,27,193..

Guo,R.;Sanders,D.F.;Smith,Z.P.;Freeman,B.D.;Paul,D.R.;McGrath,J.E.Synthesisandcharacterizationofthermallyrearranged(TR)polymers:influenceofortho-positionedfunctionalgroupsofpolyimideprecursorsonTRprocessandgastransportproperties.J. Mater. Chem. A.2013,1,262−272..

Butnaru,I.;Sava,I.;Damaceanu,M.D.Exploringtheimpactoftriphenylmethaneincorporationonphysicalpropertiesofpolyimideswithemphasisonopticalandhalochromicbehaviour.Polymer2020,200,122621..

Hariharan,R.;Sarojadevi,M.Synthesisandpropertiesoforganosolublepolyimidesderivedfrombis(4-amino-3,5-dimethylphenyl)halophenylmethaneandvariousdianhydrides.J. Appl. Polym. Sci.2006,102,4127−4135..

Hamciuc,C.;Carja,I.D.;Hamciuc,E.;Vlad-Bubulac,T.;Ignat,M.Phthalonitrile-containingaromaticpolyimidethinfilmswithnano-actuationproperties.Polym. Adv. Technol.2013,24,258..

Bejan,A.E.;Constantin,C.P.;Damaceanu,M.D.Evidenceofdiimidestructurevariationonoverallperformanceofelectro(fluoro)chromicdevicesintegratingversatiletriphenylamine-basedpolyimides.Mater. Today Chem.2022,26,101100..

Chiriac,A.P.;Damaceanu,M.D.Anovelapproachtowardscrown-ethermodifiedpolyimideswithaffinityforalkalimetalionsrecognition.J. Mol. Liq.2021,322,114929..

Huang,X.;Huang,W.;Liu,J.;Meng,L.;YanD.Synthesisofhighlysolubleandtransparentpolyimides.Polym. Int.2012,61,1503..

Tapaswi,P.K.;Choi,M.C.;Jeong,K.M.;Ando,S.;Ha,C.S.Transparentaromaticpolyimidesderivedfromthiophenyl-substitutedbenzidineswithhighrefractiveindexandsmallbirefringence.Macromolecules2015,48,3462−3474..

Kim,S.D.;Kim,S.Y.;Chung,I.S.Solubleandtransparentpolyimidesfromunsymmetricaldiaminecontainingtwotrifluoromethylgroups.J. Polym. Sci., Part A: Polym. Chem.2013,51,4413−4422..

Wang,C.;Chen,W.;Chen,Y.;Zhao,X.;Li,J.;Ren,Q.Synthesisandpropertiesofnewfluorene-basedpolyimidescontainingtrifluoromethylandisopropylsubstituents.Macromol. Chem. Phys.2014,144,553−559..

Wu,Y.;Ji,J.;Huang,H.;Liu,S.;Zhao,J.Facilesynthesisofacyloxy-containingfluorene-basedCardopolyimideswithhighopticaltransparency,fluorescenceandlowdielectricconstant.React. Funct. Polym.2021,166,104979..

Yuan,C.;Sun,Z.;Wang,Y.Synthesisandcharacterizationofanovelorgano-solublepolyimidecontaininghydroxylandbis-tert-butylsubstitutedtriphenylpyridineunits.J. Polym. Res.2020,27,220..

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Modified Triphenylmethane-based Polyimides with Improved Optical, Dielectric and Solubility Properties via Post-Polymerization Modification

DOI：10.1007/s10118-023-3018-z

摘要

Abstract

关键词

Keywords

references