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Self-assembled nanoparticles of p-phenylenediacetonitrile derivatives with fluorescence turn-on

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Abstract

Absence of emission concentration quenching accompanied by high emission efficiency in a solid state is highly challenging though very attractive, for example, for fabrication of solid state light emitters or fluorescent organic nanoparticles (FONs). Here, formation of FONs based on novel p-phenylenediacetonitrile derivatives by re-precipitation method in aqueous solutions is demonstrated. The exceptionality of the derivatives employed is manifested by nitrile groups-induced steric hindrance effects inhibiting concentration quenching of emission. Consisting of different size and polarity end-groups, phenyl groups in one compound and hexyl-carbazolyl in another, the derivatives were examined and compared in regard to nanoparticle formation morphology, size tunability, spectral signatures, and fluorescence turn-on efficiency. The variation of solvent/non-solvent ratio allowed to achieve tuning of the FON sizes from 55 nm up to 360 nm and resulted in maximal fluorescence on/off ratio of 38. Spectrally resolved confocal fluorescence microscopy revealed somewhat different molecule arrangement in different FONs suggesting dominant amorphous-like phase, which was confirmed by small angle X-ray scattering measurements. The FONs were verified to be stable against degradation or conglomeration into larger clusters at least over a couple of months thus implying their feasibility for practical applications. Finally, potential application of the fluorescent p-phenylenediacetonitrile nanoparticles for organic vapor sensing via fluorescence on/off switching was demonstrated.

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Acknowledgments

The research was funded by a grant (No. MIP-073/2011) from the Research Council of Lithuania. Dr. A. Gruodis is acknowledged for performing DFT calculations. Dr. A. Kadys is acknowledged for help in FE-SEM measurements. Dr. R. Juškėnas is thanked for performing SAXS measurements.

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Authors and Affiliations

  1. Institute of Applied Research, Vilnius University, Saulėtekio 9-III, LT-10222, Vilnius, Lithuania

    Karolis Kazlauskas, Arūnas Miasojedovas, Darius Dobrovolskas & Saulius Juršėnas

  2. Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų 19, LT-50254, Kaunas, Lithuania

    Eglė Arbačiauskienė, Vytautas Getautis & Algirdas Šačkus

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  1. Karolis Kazlauskas
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  2. Arūnas Miasojedovas
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  3. Darius Dobrovolskas
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  4. Eglė Arbačiauskienė
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  5. Vytautas Getautis
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  6. Algirdas Šačkus
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  7. Saulius Juršėnas
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Correspondence to Karolis Kazlauskas.

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Kazlauskas, K., Miasojedovas, A., Dobrovolskas, D. et al. Self-assembled nanoparticles of p-phenylenediacetonitrile derivatives with fluorescence turn-on. J Nanopart Res 14, 877 (2012). https://doi.org/10.1007/s11051-012-0877-6

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  • DOI: https://doi.org/10.1007/s11051-012-0877-6

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