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Erschienen in: Journal of Materials Science 14/2016

25.04.2016 | Original Paper

Facile synthesis of graphene oxide sheet-immobilized perylene diimide radical anion salt and its optical response to different solvents and pH values

verfasst von: Enfang He, Jianmin Wang, Hai Xu, Zemin He, Hailong Wang, Hang Zhao, Yingying Zhang, Ruijun Zhang, Haiquan Zhang

Erschienen in: Journal of Materials Science | Ausgabe 14/2016

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Abstract

Graphene oxide/reduced perylene diimide radical anion hybrid (GO/rSFPDI) with high dispersibility in polar organic solvents has been flexibly developed using N,N′-diethylhexyl-1-bromo-7-pentafluorophenox-perylene diimide (SFPDI). The interaction of the GO with the SFPDI suggested the catalysis of perylene diimide (SFPDI) to reduced perylene diimide radical anion (rSFPDI). The successful preparation of GO/rSFPDI was confirmed via FT-IR, Raman, UV–Vis absorption spectrum, XRD, and SEM. Compared to the two neutral SFPDI and GO, GO/rSFPDI exhibited a novel lower energy electronic transition (max. at 700 nm) in addition to the solvatochromism and characteristics of spectral response to pH. Moreover, the fluorescence emission spectrum of GO/rSFPDI shows strong fluorescence quenching in dilute solution.

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Literatur
1.
Zurück zum Zitat Dreyer DR, Park S, Bielawski CW, Ruoff RS (2010) The chemistry of graphene oxide. Chem Soc Rev 39:228–240CrossRef Dreyer DR, Park S, Bielawski CW, Ruoff RS (2010) The chemistry of graphene oxide. Chem Soc Rev 39:228–240CrossRef
2.
Zurück zum Zitat Ren ZJ, Sun DM, Zhang JM, Yan SK (2012) Tetrachloroperylene diimide functionalized reduced graphene oxide sheets and their I–V behavior by current sensing atomic force microscopy. Mater Chem 22:18839–18846CrossRef Ren ZJ, Sun DM, Zhang JM, Yan SK (2012) Tetrachloroperylene diimide functionalized reduced graphene oxide sheets and their IV behavior by current sensing atomic force microscopy. Mater Chem 22:18839–18846CrossRef
3.
Zurück zum Zitat Xu YX, Shi GQ (2011) Assembly of chemically modified graphene: methods and applications. J Mater Chem 21:3311–3323CrossRef Xu YX, Shi GQ (2011) Assembly of chemically modified graphene: methods and applications. J Mater Chem 21:3311–3323CrossRef
4.
Zurück zum Zitat Barrejon M, Vizuete M, Gomez-Escalonilla MJ, Fierro JLG, Berlanga I, Zamora F, Abellan G, Atienzar P, Nierengarten JF, García H, Langa F (2014) A photoresponsive graphene oxide–C60 conjugate. Chem Commun 50:9053–9055CrossRef Barrejon M, Vizuete M, Gomez-Escalonilla MJ, Fierro JLG, Berlanga I, Zamora F, Abellan G, Atienzar P, Nierengarten JF, García H, Langa F (2014) A photoresponsive graphene oxide–C60 conjugate. Chem Commun 50:9053–9055CrossRef
5.
Zurück zum Zitat Würthner F (2004) Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem Commun 17:1564–1579CrossRef Würthner F (2004) Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures. Chem Commun 17:1564–1579CrossRef
6.
Zurück zum Zitat Pron A, Reghu RR, Rybakiewicz R, Cybulski H, Djurado D, Grazulevicius JV, Zagorska M, Kulszewicz-Bajer I, Verilhac JM (2011) Triarylamine substituted arylene bisimides as solution processable organic semiconductors for field effect transistors. J Phys Chem C 115:15008–15017CrossRef Pron A, Reghu RR, Rybakiewicz R, Cybulski H, Djurado D, Grazulevicius JV, Zagorska M, Kulszewicz-Bajer I, Verilhac JM (2011) Triarylamine substituted arylene bisimides as solution processable organic semiconductors for field effect transistors. J Phys Chem C 115:15008–15017CrossRef
7.
Zurück zum Zitat Chen KY, Fang TC, Chang MZ (2012) Synthesis photophysical and electrochemical properties of 1-aminoperylene bisimides. Dyes Pigm 92:517–523CrossRef Chen KY, Fang TC, Chang MZ (2012) Synthesis photophysical and electrochemical properties of 1-aminoperylene bisimides. Dyes Pigm 92:517–523CrossRef
8.
Zurück zum Zitat Schmidt R, Oh JH, Sun YS, Deppisch M, Krause AM, Radacki K, Braunschweig H, Könemann M, Erk P, Bao ZN, Würthner F (2009) High-performance air-stable n-channel organic thin film transistors based on halogenated perylene bisimide semiconductors. J Am Chem Soc 113:6215–6228CrossRef Schmidt R, Oh JH, Sun YS, Deppisch M, Krause AM, Radacki K, Braunschweig H, Könemann M, Erk P, Bao ZN, Würthner F (2009) High-performance air-stable n-channel organic thin film transistors based on halogenated perylene bisimide semiconductors. J Am Chem Soc 113:6215–6228CrossRef
9.
Zurück zum Zitat Zhan XW, Tan ZA, Domercq B, And Z, Zhang X, Barlow S, Li YF, Zhu DB, Kippelen B, Marder SR (2007) A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells. J Am Chem Soc 23:7246–7247CrossRef Zhan XW, Tan ZA, Domercq B, And Z, Zhang X, Barlow S, Li YF, Zhu DB, Kippelen B, Marder SR (2007) A high-mobility electron-transport polymer with broad absorption and its use in field-effect transistors and all-polymer solar cells. J Am Chem Soc 23:7246–7247CrossRef
10.
Zurück zum Zitat Supur M, Ohkubo K, Fukuzumi S (2014) Photoinduced charge separation in ordered self-assemblies of perylenediimide–graphene oxide hybrid layers. Chem Commun 50:13359–13361CrossRef Supur M, Ohkubo K, Fukuzumi S (2014) Photoinduced charge separation in ordered self-assemblies of perylenediimide–graphene oxide hybrid layers. Chem Commun 50:13359–13361CrossRef
11.
Zurück zum Zitat Yu HJ, Joo PJ, Lee DY, Kim BS, Oh JH (2015) Photoinduced charge-carrier dynamics of phototransistors based on perylene diimide/reduced graphene oxide core/shell p–n junction nanowires. Adv Opt Mater 3:241–247CrossRef Yu HJ, Joo PJ, Lee DY, Kim BS, Oh JH (2015) Photoinduced charge-carrier dynamics of phototransistors based on perylene diimide/reduced graphene oxide core/shell p–n junction nanowires. Adv Opt Mater 3:241–247CrossRef
12.
Zurück zum Zitat Zhao H, Zhang YY, Xu H, He ZM, Zhang ZL, Zhang HQ (2015) Synthesis and properties of perylene diimide dyes bearing asymmetrical and symmetrical phenoxy substituents at bay positions. Tetrahedron 71:7752–7757CrossRef Zhao H, Zhang YY, Xu H, He ZM, Zhang ZL, Zhang HQ (2015) Synthesis and properties of perylene diimide dyes bearing asymmetrical and symmetrical phenoxy substituents at bay positions. Tetrahedron 71:7752–7757CrossRef
13.
Zurück zum Zitat Kumar Y, Kumar S, Keshri SK, Shukla J, Singh SS, Thakur TS, Denti M, Facchetti A, Mukhopadhyay P (2016) Synthesis of octabromoperylene dianhydride and diimides: evidence of halogen bonding and semiconducting properties. Org Lett 18:472–475CrossRef Kumar Y, Kumar S, Keshri SK, Shukla J, Singh SS, Thakur TS, Denti M, Facchetti A, Mukhopadhyay P (2016) Synthesis of octabromoperylene dianhydride and diimides: evidence of halogen bonding and semiconducting properties. Org Lett 18:472–475CrossRef
14.
Zurück zum Zitat Chen Z, Debije MG, Debaerdemaeker T, Osswald P, Würthner F (2004) Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors: studies on structural, electrochemical and charge transport properties. ChemPhysChem 1:137–140CrossRef Chen Z, Debije MG, Debaerdemaeker T, Osswald P, Würthner F (2004) Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors: studies on structural, electrochemical and charge transport properties. ChemPhysChem 1:137–140CrossRef
15.
Zurück zum Zitat Seifert S, Schmidt D, Würthner F (2015) An ambient stable core-substituted perylene bisimide dianion: isolation and single crystal structure analysis. Chem Sci 6:1663–1667CrossRef Seifert S, Schmidt D, Würthner F (2015) An ambient stable core-substituted perylene bisimide dianion: isolation and single crystal structure analysis. Chem Sci 6:1663–1667CrossRef
16.
Zurück zum Zitat Schmidt D, Bialas D, Würthner F (2015) Ambient stable zwitterionic perylene bisimide-centered radical. Angew Chem 127:3682–3685CrossRef Schmidt D, Bialas D, Würthner F (2015) Ambient stable zwitterionic perylene bisimide-centered radical. Angew Chem 127:3682–3685CrossRef
17.
Zurück zum Zitat Niyogi S, Bekyarova E, Itkis ME, Zhang H, Sheppard K, Hicks J, Sprinkle M, Berger C, Lau CN, DeHeer WA, Conrad EH, Haddon RC (2010) Spectroscopy of covalently functionalized graphene. Nano Lett 10:4061–4065CrossRef Niyogi S, Bekyarova E, Itkis ME, Zhang H, Sheppard K, Hicks J, Sprinkle M, Berger C, Lau CN, DeHeer WA, Conrad EH, Haddon RC (2010) Spectroscopy of covalently functionalized graphene. Nano Lett 10:4061–4065CrossRef
18.
Zurück zum Zitat Stankovich S, Dikin DE, Compton OC, Dommett GH, Ruoff RS, Nguyen ST (2010) Systematic post-assembly modification of graphene oxide paper with primary alkylamines. Chem Mater 22:4153–4158CrossRef Stankovich S, Dikin DE, Compton OC, Dommett GH, Ruoff RS, Nguyen ST (2010) Systematic post-assembly modification of graphene oxide paper with primary alkylamines. Chem Mater 22:4153–4158CrossRef
19.
Zurück zum Zitat Yanga YQ, Kang MM, Fanga SM, Wang MH, He LH, Zhao JH, Zhang HZ, Zhang ZH (2015) Electrochemical biosensor based on three-dimensional reduced graphene oxide and polyaniline nanocomposite for selective detection of mercury ions. Sens Actuators B 214:63–69CrossRef Yanga YQ, Kang MM, Fanga SM, Wang MH, He LH, Zhao JH, Zhang HZ, Zhang ZH (2015) Electrochemical biosensor based on three-dimensional reduced graphene oxide and polyaniline nanocomposite for selective detection of mercury ions. Sens Actuators B 214:63–69CrossRef
20.
Zurück zum Zitat Li XL, Zhang Q, Zhang XL, Li HT, Huang JM (2015) In-situ polymerization of polyaniline on the surface of graphene oxide for high electrochemical capacitance. Thin Solid Films 584:348–352CrossRef Li XL, Zhang Q, Zhang XL, Li HT, Huang JM (2015) In-situ polymerization of polyaniline on the surface of graphene oxide for high electrochemical capacitance. Thin Solid Films 584:348–352CrossRef
21.
Zurück zum Zitat Würthner F, Sautter A, Schmidt D, Weber PJ (2001) Fluorescent and electroactive cyclic assemblies from perylene tetracarboxylic acid bisimide ligands and metal phosphine triflates. Chem Eur J 4:894–902CrossRef Würthner F, Sautter A, Schmidt D, Weber PJ (2001) Fluorescent and electroactive cyclic assemblies from perylene tetracarboxylic acid bisimide ligands and metal phosphine triflates. Chem Eur J 4:894–902CrossRef
22.
Zurück zum Zitat Marcon RO, Brochsztain S (2009) Aggregation of 3,4,9,10-perylene diimide radical anions and anions generated by reduction with dithionite in aqueous solutions. J Phys Chem A 113:1747–1752CrossRef Marcon RO, Brochsztain S (2009) Aggregation of 3,4,9,10-perylene diimide radical anions and anions generated by reduction with dithionite in aqueous solutions. J Phys Chem A 113:1747–1752CrossRef
23.
Zurück zum Zitat Shirman E, Ustinov A, Ben-Shitrit N, Weissman H, Iron MA, Cohen R, Rybtchinski B (2008) Stable aromatic dianion in water. J Phys Chem B 112:8855–8858CrossRef Shirman E, Ustinov A, Ben-Shitrit N, Weissman H, Iron MA, Cohen R, Rybtchinski B (2008) Stable aromatic dianion in water. J Phys Chem B 112:8855–8858CrossRef
24.
Zurück zum Zitat Osaheni JA, Jenekhe SA (1994) Efficient blue luminescence of a conjugated polymer exciplex. Macromolecules 27:739–742CrossRef Osaheni JA, Jenekhe SA (1994) Efficient blue luminescence of a conjugated polymer exciplex. Macromolecules 27:739–742CrossRef
25.
Zurück zum Zitat Shepherd WEB, Platt AD, Kendrick MJ, Loth MA, Anthony JE, Ostroverkhova O (2011) Energy transfer and exciplex formation and their impact on exciton and charge carrier dynamics in organic films. J Phys Chem Lett 2:362–366CrossRef Shepherd WEB, Platt AD, Kendrick MJ, Loth MA, Anthony JE, Ostroverkhova O (2011) Energy transfer and exciplex formation and their impact on exciton and charge carrier dynamics in organic films. J Phys Chem Lett 2:362–366CrossRef
26.
Zurück zum Zitat Kong CC, Peng MH, Shen H (2015) A novel D-A type terpyridine-based carbazole Zn(II) complex with enhanced two-photon absorption and its bioimaging application. Dyes Pigm 120:328–334CrossRef Kong CC, Peng MH, Shen H (2015) A novel D-A type terpyridine-based carbazole Zn(II) complex with enhanced two-photon absorption and its bioimaging application. Dyes Pigm 120:328–334CrossRef
27.
Zurück zum Zitat Zhao H, Zhang YY, Xu H, He EF, Zhang ZL, Peng QM, Zhang RJ, Zhang HQ (2015) Perylene diimide dye/layered carbide charge transfer composite: design, synthesis, and photophysical properties. Mater Lett 161:208–211CrossRef Zhao H, Zhang YY, Xu H, He EF, Zhang ZL, Peng QM, Zhang RJ, Zhang HQ (2015) Perylene diimide dye/layered carbide charge transfer composite: design, synthesis, and photophysical properties. Mater Lett 161:208–211CrossRef
28.
Zurück zum Zitat Ai L, Jiang J (2012) Removal of methylene blue from aqueous solution with self-assembled cylindrical graphene–carbon nanotube hybrid. Chem Eng J 192:156–163CrossRef Ai L, Jiang J (2012) Removal of methylene blue from aqueous solution with self-assembled cylindrical graphene–carbon nanotube hybrid. Chem Eng J 192:156–163CrossRef
29.
Zurück zum Zitat Gao H, Sun Y, Zhou J, Xu R, Duan H (2013) Mussel-inspired synthesis of polydopamine-functionalized graphene hydrogel as reusable adsorbents for water purification. ACS Appl Mater Interfaces 5:425–432CrossRef Gao H, Sun Y, Zhou J, Xu R, Duan H (2013) Mussel-inspired synthesis of polydopamine-functionalized graphene hydrogel as reusable adsorbents for water purification. ACS Appl Mater Interfaces 5:425–432CrossRef
30.
Zurück zum Zitat Cheng C, Deng J, Lei B, He A, Zhang X, Ma L, Li S, Zhao C (2013) Toward 3D graphene oxide gels based adsorbents for high efficient water treatment via the promotion of biopolymers. J Hazard Mater 263:467–478CrossRef Cheng C, Deng J, Lei B, He A, Zhang X, Ma L, Li S, Zhao C (2013) Toward 3D graphene oxide gels based adsorbents for high efficient water treatment via the promotion of biopolymers. J Hazard Mater 263:467–478CrossRef
Metadaten
Titel
Facile synthesis of graphene oxide sheet-immobilized perylene diimide radical anion salt and its optical response to different solvents and pH values
verfasst von
Enfang He
Jianmin Wang
Hai Xu
Zemin He
Hailong Wang
Hang Zhao
Yingying Zhang
Ruijun Zhang
Haiquan Zhang
Publikationsdatum
25.04.2016
Verlag
Springer US
Erschienen in
Journal of Materials Science / Ausgabe 14/2016
Print ISSN: 0022-2461
Elektronische ISSN: 1573-4803
DOI
https://doi.org/10.1007/s10853-016-9885-8

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