nach oben

Erschienen in:

01.07.2014 | Research Paper

Ferroelectric nanofibers with an embedded optically nonlinear benzothiazole derivative

verfasst von: Rosa M. F. Baptista, Dmitry Isakov, M. Manuela M. Raposo, Michael Belsley, Igor Bdikin, Andrei L. Kholkin, Susana P. G. Costa, Etelvina de Matos Gomes

Erschienen in: Journal of Nanoparticle Research | Ausgabe 7/2014

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config

KI-gestützte Suche

Aus

Abstract

We report measurements of the molecular first hyperpolarizability, thermal stability, photophysical, piezoelectric, and ferroelectric properties of a benzothiazole derivative bearing an arylthiophene π-conjugated bridge both in solution and when embedded into a poly (l-lactic acid) matrix in the form of electrospun fibers with an average diameter of roughly 500 nm. The embedded nanocrystalline phenylthienyl-benzothiazole with crystal sizes of about 1.4 nm resulted in a good piezoelectric response from these functionalized electrospun fibers, indicative of a polar crystalline structure.

Vorheriger Artikel Synthesis, annealing effect and magnetic behavior of TbMnO3 nanoparticles

Nächster Artikel Green and facile synthesis of water-soluble ZnS quantum dots nanohybrids using chitosan derivative ligands

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

über 102.000 Bücher
über 537 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Finance + Banking
Management + Führung
Marketing + Vertrieb
Maschinenbau + Werkstoffe
Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

über 67.000 Bücher
über 390 Zeitschriften

aus folgenden Fachgebieten:

Automobil + Motoren
Bauwesen + Immobilien
Business IT + Informatik
Elektrotechnik + Elektronik
Energie + Nachhaltigkeit
Maschinenbau + Werkstoffe

Jetzt Wissensvorsprung sichern!

Jetzt informieren

Albert IDL, Marks TJ, Ratner MA (1997) Large molecular hyperpolarizabilities. Quantitative analysis of aromaticity and auxiliary donor-acceptor effects. J Am Chem Soc 119:6575–6582. doi:10.1021/ja962968u CrossRef

Balke N, Bdikin I, Kalinin S, Kholkin A (2009) Electromechanical imaging and spectroscopy of ferroelectric and piezoelectric materials: state of the art and prospects for the future. J Am Ceram Soc 92:1629–1647. doi:10.1111/j.1551-2916.2009.03240.x CrossRef

Batista RMF, Costa SPG, Raposo MMM (2004) Synthesis of new fluorescent 2-(2′,2′′-bithienyl)-1,3-benzothiazoles. Tetrahedron Lett 45:2825–2828. doi:10.1016/j.tetlet.2004.02.048 CrossRef

Batista RMF, Costa SPG, Malheiro EL et al (2007) Synthesis and characterization of new thienylpyrrolyl-benzothiazoles as efficient and thermally stable nonlinear optical chromophores. Tetrahedron 63:4258–4265CrossRef

Breitung EM, Shu C-F, McMahon RJ (2000) Thiazole and thiophene analogues of donor-acceptor stilbenes: molecular hyperpolarizabilities and structure-property relationships. J Am Chem Soc 122:1154–1160. doi:10.1021/ja9930364 CrossRef

Coe BJ, Harris JA, Hall JJ et al (2006) Synthesis and quadratic nonlinear optical properties of salts containing benzothiazolium electron-acceptor groups. Chem Mater 18:5907–5918. doi:10.1021/cm061594t CrossRef

Coelho P, Castro MCR, Fonseca AMC et al (2012a) Enhancement of the photochromic switching speed of bithiophene azo dyes. Tetrahedron Lett 53:4502–4506. doi:10.1016/j.tetlet.2012.05.166 CrossRef

Coelho P, Castro MCR, Fonseca AMC, Raposo MMM (2012b) Photoswitching in azo dyes bearing thienylpyrrole and benzothiazole heterocyclic systems. Dye Pigment 92:745–748. doi:10.1016/j.dyepig.2011.06.019 CrossRef

Coelho P, Sousa CM, Castro MCR et al (2013) Fast thermal cis-trans isomerization of heterocyclic azo dyes in PMMA polymers. Opt Mater 35:1167–1172. doi:10.1016/j.optmat.2013.01.007 CrossRef

Costa SPG, Ferreira JA, Kirsch G, Oliveira-Campos AMF (1997) New fluorescent 1,3-benzothiazoles by the reaction of heterocyclic aldehydes with ortho-aminobenzenethiol. J Chem Res (S) 314–315; (M) 2001–2013. doi:10.1039/A702605F

Costa SPG, Batista RMF, Cardoso P et al (2006) 2-Arylthienyl-substituted 1,3-benzothiazoles as new nonlinear optical chromophores. Eur J Org Chem. doi:10.1002/ejoc.200600059

Cui Y, Qian G, Chen L, Wang Z, Gao J, Wang M (2006) Enhanced thermal stability of dipole alignment in inorganic-organic hybrid films containing benzothiazole chromophore. J Phys Chem B 110:4105–4110. doi:10.1021/jp057146a CrossRef

Fu H-Y, Gao X-d, Zhong G-y et al (2009a) Synthesis and electroluminescence properties of benzothiazole derivatives. J Lumin 129:1207–1214. doi:10.1016/j.jlumin.2009.06.004 CrossRef

Fu H-Y, Sun X-Y, Gao X-d et al (2009b) Synthesis and characterization of benzothiazole derivatives for blue electroluminescent devices. Synth Met 159:254–259. doi:10.1016/j.synthmet.2008.09.013 CrossRef

Garcia-Amorós J, Castro MCR, Coelho P, Raposo MMM, Velasco D (2013) New heterocyclic systems to afford microsecond green-light isomerisable azo dyes and their use as fast molecular photochromic switches. Chem Commun 49:11427–11429. doi:10.1039/C3CC46736H CrossRef

Garcia-Amorós J, Reig M, Castro MCR, Cuadrado A, Raposo MMM, Velasco D (2014) Molecular photo-oscillators based on highly accelerated heterocyclic azo dyes in nematic liquid crystals. Chem Commun 50(51):6704–6706. doi:10.1039/C4CC01450B CrossRef

Hrobarik P, Zahradnik P, Fabian WMF (2004) Computational design of benzothiazole-derived push-pull dyes with high molecular quadratic hyperpolarizabilities. Phys Chem Chem Phys 6:495–502. doi:10.1039/B314150K CrossRef

Hrobárik P, Hrobarikova V, Sigmundova I et al (2011) Benzothiazoles with tunable electron-withdrawing strength and reverse polarity: a route to triphenylamine-based chromophores with enhanced two-photon absorption. J Org Chem 76:8726–8736. doi:10.1021/jo201411t CrossRef

Hrobárik P, Sigmundova I, Zahradník P et al (2010) Molecular engineering of benzothiazolium salts with large quadratic hyperpolarizabilities: can auxiliary electron-withdrawing groups enhance nonlinear optical responses? J Phys Chem C 114:22289–22302. doi:10.1021/jp108623d CrossRef

Hrobáriková V, Hrobárik P, Gajdoš P et al (2010) Benzothiazole-based fluorophores of donor-π-acceptor-π-donor type displaying high two-photon absorption. J Org Chem 75:3053–3068. doi:10.1021/jo100359q CrossRef

Isakov D, de Matos Gomes E, Belsley MS et al (2010a) High nonlinear optical anisotropy of urea nanofibers. Europhys Lett 91:28007. doi:10.1209/0295-5075/91/28007 CrossRef

Isakov DV, de Matos Gomes E, Almeida BG et al (2010b) Piezoresponse force microscopy studies of the triglycine sulfate-based nanofibers. J Appl Phys 108:042011–042014. doi:10.1063/1.3474966 CrossRef

Isakov DV, de Matos Gomes E, Vieira LG et al (2011a) Oriented single-crystal-like molecular arrangement of optically nonlinear 2-methyl-4-nitroaniline in electrospun nanofibers. ACS Nano 5:73–78. doi:10.1021/Nn101413x CrossRef

Isakov D, de Matos Gomes E, Bdikin I et al (2011b) Production of polar β-glycine nanofibers with enhanced nonlinear optical and piezoelectric properties. Cryst Growth Design 11:4288–4291. doi:10.1021/cg2009336 CrossRef

Isakov D, de Matos Gomes E, Belsley MS et al (2012) Strong enhancement of second harmonic generation in 2-methyl-4-nitroaniline nanofibers. Nanoscale 4:4978–4982. doi:10.1039/C2NR30771E CrossRef

Isakov DV, de Matos Gomes E, Almeida BG et al (2014) Energy harvesting from nanofibers of hybrid organic ferroelectric dabcoHReO₄. Appl Phys Lett 104:032907. doi:10.1063/1.4862437 CrossRef

Jin XF, Cui YJ, Gao Jk et al (2009) High thermally stable hybrid nonlinear optical films containing heterocycle chromophores. Thin Solid Films 517:5079–5083. doi:10.1016/j.tsf.2009.03.092 CrossRef

Kaatz P, Shelton DP (1996) Polarized hyper-Rayleigh light scattering measurements of nonlinear optical chromophores. J Chem Phys 105:3918–3929. doi:10.1063/1.472264 CrossRef

Kariduraganavar MY, Tambe SM, Tasaganva RG et al (2011) Studies on nonlinear optical polyurethanes containing heterocyclic chromophores. J Mol Struct 987:158–165. doi:10.1016/j.molstruc.2010.12.010 CrossRef

Kuwabara J, Namekawa T, Haga M, Kanbara T (2012) Luminescent Ir(III) complexes containing benzothiazole-based tridentate ligands: synthesis, characterization, and application to organic light-emitting diodes. Dalton Trans 41:44–46. doi:10.1039/C1dt11560j CrossRef

Li D, Wang Y, Xia Y (2003) Electrospinning of polymeric and ceramic nanofibers as uniaxially aligned arrays. Nano Lett 3:1167–1171. doi:10.1021/nl0344256 CrossRef

Li SPY, Tang TSM, Yiu KSM, Lo KKW (2012) Cyclometalated iridium(III)-polyamine complexes with intense and long-lived multicolor phosphorescence: synthesis, crystal structure, photophysical behavior, cellular uptake, and transfection properties. Chem Eur J 18:13342–13354. doi:10.1002/chem.201200979 CrossRef

Liu Y, Guo H, Zhao J (2011) Ratiometric luminescent molecular oxygen sensors based on uni-luminophores of CN Pt(II)(acac) complexes that show intense visible-light absorption and balanced fluorescence/phosphorescence dual emission. Chem Commun 47:11471–11473. doi:10.1039/C1CC14582G CrossRef

Mabrouk A, Azazi A, Alimi K (2010) On the properties of new benzothiazole derivatives for organic light emitting diodes (OLEDs): a comprehensive theoretical study. J Phys Chem Solids 71:1225–1235. doi:10.1016/j.jpcs.2010.04.020 CrossRef

Miller RD, Lee VY, Moylan CR (1994) Substituted azole derivatives as nonlinear-optical chromophores. Chem Mater 6:1023–1032. doi:10.1021/Cm00043a026 CrossRef

Mishra A, Ma CQ, Bauerle P (2009) Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications. Chem Rev 109:1141–1276. doi:10.1021/cr8004229 CrossRef

Morris JV, Mahaney MA, Huber JR (1976) Fluorescence quantum yield determinations. 9,10-Diphenylanthracene as a reference-standard in different solvents. J Phys Chem 80:969–974. doi:10.1021/j100550a010 CrossRef

Nye JF (2000) Physical properties of crystals: their representation by tensors and matrices. Clarendon Press, Oxford

Oudar JL (1977) Optical nonlinearities of conjugated molecules. Stilbene derivatives and highly polar aromatic compounds. J Chem Phys 67:446–457. doi:10.1063/1.434888 CrossRef

Oudar JL, Chemla DS (1977) Hyperpolarizabilities of the nitroanilines and their relations to the excited state dipole moment. J Chem Phys 66:2664–2668. doi:10.1063/1.434213 CrossRef

Persano L, Dagdeviren C, Su Y et al (2013) High performance piezoelectric devices based on aligned arrays of nanofibers of poly(vinylidenefluoride-co-trifluoroethylene). Nat Commun 4:1633. doi:10.1038/ncomms2639 CrossRef

Pina J, Seixas de Melo S, Batista RMF et al (2007) Spectral and photophysical characterization of donor-pi-acceptor arylthienyl- and bithienyl-benzothiazole derivatives in solution and solid state. Phys Chem A 111:8574–8578. doi:10.1021/Jp0730646 CrossRef

Pina J, Seixas de Melo S, Batista RMF et al (2010) The influence of the relative position of the thiophene and pyrrole rings in donor-acceptor thienylpyrrolyl-benzothiazole derivatives. A photophysical and theoretical investigation. Phys Chem Chem Phys 12:9719–9725. doi:10.1039/C002434a CrossRef

Raposo MMM, Castro MCR, Schellenberg P et al (2011a) Design, synthesis, and characterization of the electrochemical, nonlinear optical properties, and theoretical studies of novel thienylpyrrole azo dyes bearing benzothiazole acceptor groups. Tetrahedron 67:5189–5198. doi:10.1016/j.tet.2011.05.053 CrossRef

Raposo MMM, Castro MCR, Belsley M, Fonseca AMC (2011b) Push pull bithiophene azo-chromophores bearing thiazole and benzothiazole acceptor moieties: synthesis and evaluation of their redox and nonlinear optical properties. Dye Pigment 91:454–465. doi:10.1016/j.dyepig.2011.05.007 CrossRef

Raposo MMM, Fonseca AMC, Castro MCR et al (2011c) Synthesis and characterization of novel diazenes bearing pyrrole, thiophene and thiazole heterocycles as efficient photochromic and nonlinear optical (NLO) materials. Dye Pigment 91:62–73. doi:10.1016/j.dyepig.2011.02.012 CrossRef

Razus AC, Birzan L, Surugiu NM et al (2007) Syntheses of azulen-1-yl-benzothiazol-2-yl diazenes. Dye Pigment 74:26–33. doi:10.1016/j.dyepig.2006.01.041 CrossRef

Reis H (2006) Problems in the comparison of theoretical and experimental hyperpolarizabilities revisited. J Chem Phys 125:014506–014509. doi:10.1063/1.2211611 CrossRef

Tao Y, Yang C, Qin J (2011) Organic host materials for phosphorescent organic light-emitting diodes. Chem Soc Rev 40:2943–2970. doi:10.1039/C0CS00160K CrossRef

Varanasi PR, Jen AK-Y, Chandrasekhar J et al (1996) The important role of heteroaromatics in the design of efficient second-order nonlinear optical molecules: theoretical investigation on push-pull heteroaromatic stilbenes. J Am Chem Soc 118:12443–12448. doi:10.1021/ja960136q CrossRef

Wang RJ, Liu D, Ren HC et al (2011) Homoleptic tris-cyclometalated iridium complexes with 2-phenylbenzothiazole ligands for highly efficient orange OLEDs. Mater Chem 21:15494–15500. doi:10.1039/C1JM10757G CrossRef

Xu XJ, Liao Y, Yu G et al (2007) Charge carrier transporting, photoluminescent, and electroluminescent properties of zinc(II)-2-(2-hydroxyphenyl)benzothiazolate complex. Chem Mater 19:1740–1748. doi:10.1021/cm062960b CrossRef

Zhang XH, Wong OY, Gao ZQ et al (2001) A new blue-emitting benzothiazole derivative for organic electroluminescent devices. Mater Sci Eng B 85:182–185. doi:10.1016/S0921-5107(01)00607-9 CrossRef

Zyss J, Oudar JL (1982) Structural dependence of nonlinear-optical properties of methyl-(2,4-dinitrophenyl)-aminopropanoate crystals. Phys Rev A 26:2016–2027. doi:10.1103/PhysRevA.26.2016 CrossRef

Titel: Ferroelectric nanofibers with an embedded optically nonlinear benzothiazole derivative
verfasst von: Rosa M. F. Baptista
Dmitry Isakov
M. Manuela M. Raposo
Michael Belsley
Igor Bdikin
Andrei L. Kholkin
Susana P. G. Costa
Etelvina de Matos Gomes
Publikationsdatum: 01.07.2014
Verlag: Springer Netherlands
Erschienen in: Journal of Nanoparticle Research / Ausgabe 7/2014
Print ISSN: 1388-0764
Elektronische ISSN: 1572-896X
DOI: https://doi.org/10.1007/s11051-014-2502-3

Premium Partner

Marktübersichten

Die im Laufe eines Jahres in der „adhäsion“ veröffentlichten Marktübersichten helfen Anwendern verschiedenster Branchen, sich einen gezielten Überblick über Lieferantenangebote zu verschaffen.

Zur Marktübersicht

Springer Professional

Abstract

Bitte loggen Sie sich ein, um Zugang zu Ihrer Lizenz zu erhalten.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Springer Professional "Technik"

Weitere Artikel der Ausgabe 7/2014

An operationalized post-normal science framework for assisting in the development of complex science policy solutions: the case of nanotechnology governance

Architecture of ZnO nanosheets and nanochips via zinc oxalato-hydrazinate complex

High-yield synthesis of uniform B, N-rich BN-C x nanoplates in mild temperatures

Targeted cancer therapy based on single-wall carbon nanohorns with doxorubicin in vitro and in vivo

Biological response to purification and acid functionalization of carbon nanotubes

Complexation of aromatic drugs with single-walled carbon nanotubes

Premium Partner

Marktübersichten