Construction of Aniline Trimer Based Conjugated Polymers through Schiff Base Reaction and Their Use as Feedstock for Infrared Stealth Coatings

Xiang-Yu Li; Li-Shuai Zong; Yi-Bo Wang; Qi Cao; Jin-Yan Wang; Xi-Gao Jian

doi:10.1007/s10118-022-2861-7

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Construction of Aniline Trimer Based Conjugated Polymers through Schiff Base Reaction and Their Use as Feedstock for Infrared Stealth Coatings

RESEARCH ARTICLE | Updated：2023-05-26

- Construction of Aniline Trimer Based Conjugated Polymers through Schiff Base Reaction and Their Use as Feedstock for Infrared Stealth Coatings
- Construction of Aniline Trimer Based Conjugated Polymers through Schiff Base Reaction and Their Use as Feedstock for Infrared Stealth Coatings
- 高分子科学（英文版） 2023年41卷第6期页码：851-858
- Affiliations：
  
  State Key Laboratory of Fine Chemicals, Liaoning High Performance Resin Engineering Research Center, Department of Polymer Science & Engineering, Dalian University of Technology, Dalian 116024, China
- Author bio：
  
  wangjinyan@dlut.edu.cn (J.Y.W.)
  jian4616@dlut.edu.cn (X.G.J.)
- Funds：
- DOI：10.1007/s10118-022-2861-7
  中图分类号：
- 收稿：2022-07-30，
  
  修回：2022-9-10，
  
  录用：2022-9-13，
  
  网络首发：2022-10-31，
  
  纸质出版：2023-06-01
- Accepted：
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Li, X. Y.; Zong, L. S.; Wang, Y. B.; Cao, Q.; Wang, J. Y.; Jian, X. G. Construction of aniline trimer based conjugated polymers through Schiff base reaction and their use as feedstock for infrared stealth coatings. Chinese J. Polym. Sci. 2023, 41, 851–858

Xiang-Yu Li, Li-Shuai Zong, Yi-Bo Wang, et al. Construction of Aniline Trimer Based Conjugated Polymers through Schiff Base Reaction and Their Use as Feedstock for Infrared Stealth Coatings[J]. Chinese Journal of Polymer Science, 2023, 41(6): 851-858.
Li, X. Y.; Zong, L. S.; Wang, Y. B.; Cao, Q.; Wang, J. Y.; Jian, X. G. Construction of aniline trimer based conjugated polymers through Schiff base reaction and their use as feedstock for infrared stealth coatings. Chinese J. Polym. Sci. 2023, 41, 851–858 DOI： 10.1007/s10118-022-2861-7.

Xiang-Yu Li, Li-Shuai Zong, Yi-Bo Wang, et al. Construction of Aniline Trimer Based Conjugated Polymers through Schiff Base Reaction and Their Use as Feedstock for Infrared Stealth Coatings[J]. Chinese Journal of Polymer Science, 2023, 41(6): 851-858. DOI： 10.1007/s10118-022-2861-7.

摘要

We employed amine-capped aniline trimer as one of the building block to construct novel Schiff-base-containing conductive polymer coatings through dialdehyde-amine polycondensation，reducing the band gap and improving the electrical conductivity of the structure was both beneficial to the reduction of infrared emissivity. The infrared emissivity of ATTPAL coatings was 0.587 at wavelength of 8-14 μm and 0.595 at wavelength of 2-22 μm.

Abstract

In order to meet the demand for infrared stealth materials in the military field

conjugated polymers containing Schiff base moieties were designed and prepared. Various dialdehyde monomers were introduced and their effect on the comprehensive properties were systematically characterized. The resulted polymers could be cast in solution to prepare polymer coatings. The coatings exhibited high thermal stability up to 400 °C at 5% weight loss

and excellent mechanical performance with high Young's modulus and hardness. The infrared emissivity values varied from 0.587 to 0.627 at wavelength of 8−14 μm and ranged from 0.595 to 0.609 at wavelength of 2−22 μm. Specifically

it was found that the ATTPAL structure with carbazole moieties had a lower band gap and better electrical conductivity by photoelectric test and DFT theoretical analysis. Meanwhile

the infrared emissivity value of ATTPAL coating was the lowest compared with

-phenyl and pyridyl containing analogues

suggesting it was potential material for the future development of infrared stealth technology. The combined results showed that reducing the band gap and improving the electrical conductivity of the structure were both beneficial to the reduction of infrared emissivity. It would positively provide new ideas for the design of infrared stealth materials.

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references

Gu,J.;Wang,W.;Yu,D.Temperaturecontrolandlowinfraredemissivitydouble-shellphasechangemicrocapsulesandtheirapplicationininfraredstealthfabric. Prog. Org. Coat. 2021 , 159 ,106439..

Pan,W.;Zhou,Y.;He,M.;Bu,X.;Ding,B.;Huang,T.;Huang,S.;Li,S.Synthesis,helicity,andlowinfraredemissivityofopticallyactivepoly( N -propargylamide)sbearingstigmasterylmoieties. J. Mol. Struct. 2017 , 1142 ,285−292..

Shi,M.;Xu,C.;Yang,Z.;Liang,J.;Wang,L.;Tan,S.;Xu,G.Achievinggoodinfrared-radarcompatiblestealthpropertyonmetamaterial-basedabsorberbycontrollingthefloatingrateofAltypeinfraredcoating. J. Alloys Compd. 2018 , 764 ,314−322..

Tan,P.;Lu,F.;Han,Y.Mid-infraredoptimizedelectroreflectivedevicebasedonPEDOT/PSS. Sol. Energy Mater. Sol. Cells 2021 , 219 ,110808..

Chang,Y.;Wang,Y.;Wang,W.;Yu,D.Highlyefficientinfraredstealthasymmetric-structurewaterbornepolyurethanecompositesprepared via one-stepdensity-drivenfillerseparationmethod. Colloids Surf. A Physicochem. Eng. Asp. 2021 , 614 ,126177..

Xu,R.;Wang,W.;Yu,D.Preparationofsilver-platedhollowglassmicrospheresanditsapplicationininfraredstealthcoatingfabrics. Prog. Org. Coat. 2019 , 131 ,1−10..

Yu,H.;Xu,G.;Shen,X.;Yan,X.;Shao,C.;Hu,C.Effectsofsize,shapeandfloatageofCuparticlesonthelowinfraredemissivitycoatings. Prog. Org. Coat. 2009 , 66 ,161−166..

Chu,H.;Zhang,Z.;Liu,Y.;Leng,J.Silverparticlesmodifiedcarbonnanotubepaper/glassfiberreinforcedpolymercompositematerialforhightemperatureinfraredstealthcamouflage. Carbon 2016 , 98 ,557−566..

Zhang,W.;Lv,D.PreparationandcharacterizationofSi/SiO 2 one-dimensionalphotoniccrystalwithultra-lowinfraredemissivityinthe3–5μmband. Optik 2020 , 202 ,163738..

Zhang,H.;Boyan,Q.U.;Jin,L.;Chao,M.A.Infraredimagingsimulationofseasurfacedetectionofunderwatervehiclethermalwaketarget. J. Appl. Opt. 2019 , 40 ,525−534..

Huang,W.;Ji,H.Effectofenvironmentalradiationonthelong-waveinfraredsignatureofcruiseaircraft. Aerosp. Sci. Technol. 2016 , 56 ,125−134..

Zhou,X.;Xin,B.;Liu,Y.Researchprogressoninfraredstealthfabric. J. Phys. Conf. Ser. 2021 , 1790 ,012058..

Fang,K.Y.;Wang,Y.J.;Zhao,Y.C.;Fang,F.Infraredstealthnanofibrouscompositeswiththermaladaptabilityandmechanicalflexibility. Compos. Sci. Technol. 2020 , 201 ,108483..

Zhang,L.;Xu,G.;Wang,L.;Wang,B.;Ren,Z.;Dou,S.;Song,S.;Pan,M.;Li,X.;Li,Y.Achievingvariableinfraredemissivitymodulationregionsofpoly(aniline)films:theeffectoffilmsurfacemorphologyontheopticaltunability. Dyes Pigm. 2021 , 187 ,109084..

Salihoglu,O.;Uzlu,H.B.;Yakar,O.;Aas,S.;Balci,O.;Kakenov,N.;Balci,S.;Olcum,S.;Suzer,S.;Kocabas,C.Graphene-basedadaptivethermalcamouflage. Nano Lett. 2018 , 18 ,4541−4548..

Lyu,J.;Liu,Z.;Wu,X.;Li,G.;Fang,D.;Zhang,X.NanofibrousKevlaraerogelfilmsandtheirphase-changecompositesforhighlyefficientinfraredstealth. ACS Nano 2019 , 13 ,2236−2245..

Zhu,Y.;Zhou,Y.;Zhang,T.;He,M.;Wang,Y.;Yang,X.;Yang,Y.Preparationandcharacterizationoflactate-intercalatedCo-Felayereddoublehydroxidesandexfoliatednanosheetfilmwithlowinfraredemissivity. Appl. Surf. Sci. 2012 , 263 ,132−138..

Zhang,M.;Yang,G.;Zhang,L.;Zhang,Y.;Yin,J.;Ma,X.;Wen,J.;Dai,L.;Wang,X.;Chen,H.;Zhang,L.;Yin,L.;Jian,X.;Zhao,X.;Deng,L.ApplicationofZrB 2 thinfilmasalowemissivityfilmathightemperature. Appl. Surf. Sci. 2020 , 527 ,146763..

Qin,Y.;Zhang,M.;Guan,Y.;Huang,X.LaserabsorptionandinfraredstealthpropertiesofAl/ATOcomposites. Ceram. Int. 2019 , 45 ,14312−14315..

Li,E.;Bai,Y.;Dong,H.;Jia,R.;Zhao,X.;Wang,R.;Bao,M.;Ma,W.InfraredradiationandthermalpropertiesofAl-dopedSrZrO 3 perovskitesforpotentialinfraredstealthcoatingmaterialsinthehigh-temperatureenvironment. Ceram. Int. 2021 , 47 ,23124−23133..

Zhang,P.;Cai,F.;Wang,G.J.;Yu,H.F.UV-Vis-NIRlight-deformableshape-memorypolyurethanedopedwithliquid-crystalmixtureandGOtowardsbiomimeticapplications. Chinese J. Polym. Sci. 2022 , 40 ,166−174..

He,Z.W.;Zhang,Q.;Li,C.X.;Han,H.T.;Lu,Y.Synthesisofthieno[3,4- b ]pyrazine-basedalternatingconjugatedpolymers via directarylationfornear-infraredOLEDapplications. Chinese J. Polym. Sci. 2022 , 40 ,138−146..

Pan,W.;He,M.;Bu,X.;Zhou,Y.;Ding,B.;Huang,T.;Huang,S.;Li,S.Microwaveabsorptionandinfraredemissivityofhelicalpolyacetylene@multiwalledcarbonnanotubescomposites. J. Mater. Sci. Mater. Electron. 2017 , 28 ,8601−8610..

Cai,J.;Han,J.;Ma,G.;Liu,X.;Wang,J.;Jian,X.Constructionofdimetal-containingdithioleneandSchiffbaseconjugatedpolymercoating:exploitingmetalcoordinationasadesignstrategyforimprovinginfraredstealthproperties. Polym. Chem. 2019 , 10 ,5839−5848..

P.;Hourquebie,P.Infraredswitchingelectroemissivedevicesbasedonhighlyconductingpolymers. Thin Solid Films 1999 , 352 ,243−248..

Wen,H.L.;Lai,B.W.;Peng,H.L.;Xiong,Z.Q.;Liu,C.B.CharacterizationandinfraredstealthypropertiesoftwoSchiff-basecompoundsderivedfrom1-amino-2-hydroxypropaneandtheircomplexes. Chinese J. Struc. Chem. 2020 , 39 ,279−286..

Yin,J.;Wang,C.;Zheng,H.;Zhang,L.;Zhang,M.;Ma,X.;Shen,T.;Zhang,W.T.;Weng,X.L.;Jiang,S.L.;Zhang,X.F.;Fan,J.F.;Deng,C.M.;Deng,L.J.PowercontrolledmicrostructureandinfraredpropertiesofairplasmasprayingbasedonYSZcoatings. Surf. Coat. Technol. 2021 , 426 ,127768..

Louet,C.;Cantin,S.;Dudon,J.P.;Aubert,P.H.;Vidal,F.;Chevrot,C.Acomprehensivestudyofinfraredreflectivityofpoly(3,4-ethylenedioxythiophene)modellayerswithdifferentmorphologiesandconductivities. Sol. Energ. Mat. Sol. C. 2015 , 143 ,141−51..

Zhang,L.;Wang,B.;Li,X.;Xu,G.;Dou,S.;Zhang,X.;Chen,X.;Zhao,J.;Zhang,K.;Li,Y.Furtherunderstandingofthemechanismsofelectrochromicdeviceswithvariableinfraredemissivitybasedonpolyanilineconductingpolymers. J. Mater. Chem. C 2019 , 7 ,9878−9891..

Ji,W.F.;Chu,C.M.;Hsu,S.C.;Lu,Y.D.;Yu,Y.C.;Santiago,K.S.;Yeh,J.M.Synthesisandcharacterizationoforgano-solubleanilineoligomer-basedelectroactivedopedwithgoldnanoparticles,andapplicationtoelectrochemicalsensingofascorbicacid. Polymer 2017 , 128 ,218−228..

Reddy,P.M.;Hsieh,S.R.;Lee,M.C.;Chang,C.J.;Pundi,A.;Chen,Y.S.;Lu,C.H.;Yeh,J.M.AnilinetrimerbasedchemicalsensorfordualresponsivedetectionofhazardousCN¯ionsandpHchanges. Dyes Pigm. 2019 , 164 ,327−334..

Tagare,J.;Dubey,D.K.;Jou,J.H.;Vaidyanathan,S.Synthesis,photophysical,theoreticalandelectroluminescencestudyoftriphenylamine-imidazolebasedbluefluorophoresforsolution-processedorganiclightemittingdiodes. Dyes Pigm. 2019 , 160 ,944−956..

Jagadeesan,S.;Mahesh,K.;Karpagam,S.Insightintotriphenylaminedonorthiazoleacceptorconjugatedoligomertoanalyzeemissionbehaviortowardsaggregationpathway. ChemistrySelect 2019 , 4 ,11196−11205..

Garbay,G.;Giraud,L.;Gali,S.M.;Hadziioannou,G.;Grau,E.;Grelier,S.;Cloutet,E.;Cramail,H.;Brochon,C.Divanillin-basedpolyazomethines:towardbiobasedandmetal-freepi-conjugatedpolymers. ACS Omega 2020 , 5 ,5176−5181..

Kovalchuk,A.I.;Kobzar,Y.L.;Tkachenko,I.M.;Kurioz,Y.I.;Tereshchenko,O.G.;Shekera,O.V.;Nazarenko,V.G.;Shevchenko,V.V.Photoactivefluorinatedpoly(azomethine)swithAzogroupsinthemainchainforopticalstorageapplicationsandcontrollingliquidcrystalorientation. ACS Appl. Polym. Mater. 2019 , 2 ,455−463..

Grivani,G.;Ghavami,A.;Eigner,V.;Dušek,M.;Khalaji,A.D.Anewoxidovanadium(IV)SchiffbasecomplexcontainingasymmetrictetradentateONN′O′Schiffbaseligand:synthesis,characterization,crystalstructuredetermination,thermalstudyandcatalyticactivity. Chin. Chem. Lett. 2015 , 26 ,779−784..

Huo,J.;Luo,B.;Chen,Y.Crystallinecovalentorganicframeworksfromtriazinenodesasporousadsorbentsfordyepollutants. ACS Omega 2019 , 4 ,22504−22513..

Han,J.;Yuan,K.;Liu,C.;Wang,J.;Jian,X.Donor-acceptorcopolymerscontainingthephthalazinone-thiophenestructuresynthesizedbyclassicalnucleophilicaromaticpolymerization. RSC Adv. 2015 , 5 ,30445−30455..

Nouruzi,N.;Dinari,M.;Mokhtari,N.;Gholipour,B.;Rostamnia,S.;Khaksar,S.;Boluki,R.Poroustriazinepolymer:anovelcatalystforthethree-componentreaction. Appl. Organomet. Chem. 2020 , 34 ,e5677..

Li,D.;Zhang,Z.;Zhao,S.;Wang,Y.;Zhang,H.Diboron-containingfluorophoreswithextendedladder-typepi-conjugatedskeletons. Dalton Trans. 2011 , 40 ,1279−85..

Liu,Z.;Bao,C.;Zhang,G.;Zhang,K.;Lei,G.;Zhang,Q.;Peng,Q.;Liu,Y.Enhancementthephotovoltaicperformanceofconjugatedpolymerbasedonsimplehead-to-headalkylthiosidechainsengineeredbithiophene. Chin. Chem. Lett. 2020 , 31 ,2459−2464..

Hsiao,S.H.;Wang,H.M.;Liao,S.H.Redox-stableandvisible/near-infraredelectrochromicaramidswithmain-chaintriphenylamineandpendent3,6-di- tert -butylcarbazoleunits. Polym. Chem. 2014 , 5 ,2473..

Mangione,M.I.;Spanevello,R.A.;Minudri,D.;Cavallo,P.;Otero,L.;Fungo,F.Electrochemicalfilmsdepositionandelectro-opticalpropertiesofbis-carbazol-triphenylamineend-capeddendrimericpolymers. Electrochim. Acta 2018 , 263 ,585−595..

Han,J.;Weng,Z.;Wu,Z.;Cai,J.;Wang,J.;Jian,X.Constructionofflexibleandstablenear-infraredabsorbingpolymerfilmscontainingnickel-bis(dithiolene)moieties via ligand-exchangepost-polymerizationmodification. Polym. Chem. 2017 , 8 ,3977−3991..

Li,Z.;Gao,X.;Hu,X.;Zhang,X.;Jia,C.;Liu,C.;Shen,L.;Zhu,H.;Cui,M.;Lu,Z.;Guo,H.Dithienylethenesfunctionalizedbytriphenyletheneanddifluoroboron β -diketonatefragments:synthesis,opticalswitchingbehaviorandfluorescentturn-onsensingforvolatileorganicamines. Dyes Pigm. 2021 , 192 ,109422..

Zgou,H.;Bouzzine,S.M.;Bouzakraoui,S.;Hamidi,M.;Bouachrine,M.Theoreticalstudyofstructuralandelectronicpropertiesofoligo(thiophene-phenylene)sincomparisonwitholigothio-phenesandoligophenylenes. Chin. Chem. Lett. 2008 , 19 ,123−126..

Larciprete,M.C.;Paoloni,S.;Orazi,N.;Mercuri,F.;Orth,M.;Gloy,Y.;Centini,M.;LiVoti,R.;Sibilia,C.Infraredemissivitycharacterizationofcarbonnanotubesdispersedpoly(ethyleneterephthalate)fibers. Int. J. Therm. Sci. 2019 , 146 ,106109..

Hu,C.;Xu,G.;Shen,X.;Shao,C.;Yan,X.Theepoxy-siloxane/Alcompositecoatingswithlowinfraredemissivityforhightemperatureapplications. Appl. Surf. Sci. 2010 , 256 ,3459−3463..

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