Side chains control dynamics and self-sorting in fluorescent organic nanoparticles

A.G. Kaeser, I. Fischer, R.J. Abbel, P. Besenius, D. Dasgupta, M.A.J. Gillissen, G. Portale, A.L. Stevens, L.M. Herz, A.P.H.J. Schenning

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Abstract

To develop fluorescent organic nanoparticles with tailored properties for imaging and sensing, full control over the size, fluorescence, stability, dynamics, and supramolecular organization of these particles is crucial. We have designed, synthesized, and fully characterized 12 nonionic fluorene co-oligomers that formed self-assembled fluorescent nanoparticles in water. In these series of molecules, the ratio of hydrophilic ethylene glycol and hydrophobic alkyl side chains was systematically altered to investigate its role on the above-mentioned properties. The nanoparticles consisting of p-conjugated oligomers containing polar ethylene glycol side chains were less stable and larger in size, while nanoparticles self-assembled from oligomers containing nonpolar pendant chains were more stable, smaller, and generally had a higher fluorescence quantum yield. Furthermore, the dynamics of the molecules between the nanoparticles was enhanced if the number of hydrophilic side chains increased. Energy transfer studies between naphthalene and benzothiadiazole fluorene co-oligomers with the same side chains showed no exchange of molecules between the particles for the apolar molecules. For the more polar systems, the exchange of molecules between nanoparticles took place at room temperature or after annealing. Self-assembled nanoparticles consisting of p-conjugated oligomers having different side chains caused self-sorting, resulting either in the formation of domains within particles or the formation of separate nanoparticles. Our results show that we can control the stability, fluorescence, dynamics, and self-sorting properties of the nanoparticles by simply changing the nature of the side chains of the p-conjugated oligomers. These findings are not only important for the field of self-assembled nanoparticles but also for the construction of well-defined multicomponent supramolecular materials in general
Original languageEnglish
Pages (from-to)408-416
JournalACS Nano
Volume7
Issue number1
DOIs
Publication statusPublished - 2013

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dynamic control
classifying
Sorting
Nanoparticles
nanoparticles
oligomers
Oligomers
Molecules
Ethylene Glycol
Fluorescence
molecules
Ethylene glycol
fluorescence
glycols
ethylene
dynamic stability
Quantum yield
Naphthalene
naphthalene
Energy transfer

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Kaeser, A. G., Fischer, I., Abbel, R. J., Besenius, P., Dasgupta, D., Gillissen, M. A. J., ... Schenning, A. P. H. J. (2013). Side chains control dynamics and self-sorting in fluorescent organic nanoparticles. ACS Nano, 7(1), 408-416. https://doi.org/10.1021/nn305477u
Kaeser, A.G. ; Fischer, I. ; Abbel, R.J. ; Besenius, P. ; Dasgupta, D. ; Gillissen, M.A.J. ; Portale, G. ; Stevens, A.L. ; Herz, L.M. ; Schenning, A.P.H.J. / Side chains control dynamics and self-sorting in fluorescent organic nanoparticles. In: ACS Nano. 2013 ; Vol. 7, No. 1. pp. 408-416.
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Kaeser, AG, Fischer, I, Abbel, RJ, Besenius, P, Dasgupta, D, Gillissen, MAJ, Portale, G, Stevens, AL, Herz, LM & Schenning, APHJ 2013, 'Side chains control dynamics and self-sorting in fluorescent organic nanoparticles', ACS Nano, vol. 7, no. 1, pp. 408-416. https://doi.org/10.1021/nn305477u

Side chains control dynamics and self-sorting in fluorescent organic nanoparticles. / Kaeser, A.G.; Fischer, I.; Abbel, R.J.; Besenius, P.; Dasgupta, D.; Gillissen, M.A.J.; Portale, G.; Stevens, A.L.; Herz, L.M.; Schenning, A.P.H.J.

In: ACS Nano, Vol. 7, No. 1, 2013, p. 408-416.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - Side chains control dynamics and self-sorting in fluorescent organic nanoparticles

AU - Kaeser, A.G.

AU - Fischer, I.

AU - Abbel, R.J.

AU - Besenius, P.

AU - Dasgupta, D.

AU - Gillissen, M.A.J.

AU - Portale, G.

AU - Stevens, A.L.

AU - Herz, L.M.

AU - Schenning, A.P.H.J.

PY - 2013

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N2 - To develop fluorescent organic nanoparticles with tailored properties for imaging and sensing, full control over the size, fluorescence, stability, dynamics, and supramolecular organization of these particles is crucial. We have designed, synthesized, and fully characterized 12 nonionic fluorene co-oligomers that formed self-assembled fluorescent nanoparticles in water. In these series of molecules, the ratio of hydrophilic ethylene glycol and hydrophobic alkyl side chains was systematically altered to investigate its role on the above-mentioned properties. The nanoparticles consisting of p-conjugated oligomers containing polar ethylene glycol side chains were less stable and larger in size, while nanoparticles self-assembled from oligomers containing nonpolar pendant chains were more stable, smaller, and generally had a higher fluorescence quantum yield. Furthermore, the dynamics of the molecules between the nanoparticles was enhanced if the number of hydrophilic side chains increased. Energy transfer studies between naphthalene and benzothiadiazole fluorene co-oligomers with the same side chains showed no exchange of molecules between the particles for the apolar molecules. For the more polar systems, the exchange of molecules between nanoparticles took place at room temperature or after annealing. Self-assembled nanoparticles consisting of p-conjugated oligomers having different side chains caused self-sorting, resulting either in the formation of domains within particles or the formation of separate nanoparticles. Our results show that we can control the stability, fluorescence, dynamics, and self-sorting properties of the nanoparticles by simply changing the nature of the side chains of the p-conjugated oligomers. These findings are not only important for the field of self-assembled nanoparticles but also for the construction of well-defined multicomponent supramolecular materials in general

AB - To develop fluorescent organic nanoparticles with tailored properties for imaging and sensing, full control over the size, fluorescence, stability, dynamics, and supramolecular organization of these particles is crucial. We have designed, synthesized, and fully characterized 12 nonionic fluorene co-oligomers that formed self-assembled fluorescent nanoparticles in water. In these series of molecules, the ratio of hydrophilic ethylene glycol and hydrophobic alkyl side chains was systematically altered to investigate its role on the above-mentioned properties. The nanoparticles consisting of p-conjugated oligomers containing polar ethylene glycol side chains were less stable and larger in size, while nanoparticles self-assembled from oligomers containing nonpolar pendant chains were more stable, smaller, and generally had a higher fluorescence quantum yield. Furthermore, the dynamics of the molecules between the nanoparticles was enhanced if the number of hydrophilic side chains increased. Energy transfer studies between naphthalene and benzothiadiazole fluorene co-oligomers with the same side chains showed no exchange of molecules between the particles for the apolar molecules. For the more polar systems, the exchange of molecules between nanoparticles took place at room temperature or after annealing. Self-assembled nanoparticles consisting of p-conjugated oligomers having different side chains caused self-sorting, resulting either in the formation of domains within particles or the formation of separate nanoparticles. Our results show that we can control the stability, fluorescence, dynamics, and self-sorting properties of the nanoparticles by simply changing the nature of the side chains of the p-conjugated oligomers. These findings are not only important for the field of self-assembled nanoparticles but also for the construction of well-defined multicomponent supramolecular materials in general

U2 - 10.1021/nn305477u

DO - 10.1021/nn305477u

M3 - Article

C2 - 23256849

VL - 7

SP - 408

EP - 416

JO - ACS Nano

JF - ACS Nano

SN - 1936-0851

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Kaeser AG, Fischer I, Abbel RJ, Besenius P, Dasgupta D, Gillissen MAJ et al. Side chains control dynamics and self-sorting in fluorescent organic nanoparticles. ACS Nano. 2013;7(1):408-416. https://doi.org/10.1021/nn305477u