A new route towards fluorescent organic nanoparticles with red-shifted emission and increased colloidal stability

Amro, Kassem; Daniel, Jonathan; Clermont, Guillaume; Bsaibess, Talia; Pucheault, Mathieu; Genin, Émilie; Vaultier, Michel; Blanchard‐Desce, Mireille

doi:10.1016/j.tet.2014.01.032

Cited by 32 publications

(35 citation statements)

References 35 publications

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“…[32][33][34][35] Recently, it was reported that triphenylmethane-based nanoparticles are excellent candidates for single particle tracking and bioimaging due to their enhanced fluorescence and second harmonic signal. [36][37][38] Molecular-based nanomaterials such as nanoGUMBOS offer a new route for designing nonlinear optical probes by combining the inherent molecular nonlinear susceptibilities with the ability to control the resulting nanoparticle size as well as molecular interactions and structural ordering.…”

Section: Introductionmentioning

confidence: 99%

Ultrafast and nonlinear spectroscopy of brilliant green-based nanoGUMBOS with enhanced near-infrared emission

Karam

Siraj

Zhang

et al. 2017

The Journal of Chemical Physics

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The synthesis, characterization, ultrafast dynamics, and nonlinear spectroscopy of 30 nm nanospheres of brilliant green-bis(pentafluoroethylsulfonyl)imide ([BG][BETI]) in water are reported. These thermally stable nanoparticles are derived from a group of uniform materials based on organic salts (nanoGUMBOS) that exhibit enhanced near-infrared emission compared with the molecular dye in water. The examination of ultrafast transient absorption spectroscopy results reveals that the overall excited-state relaxation lifetimes of [BG][BETI] nanoGUMBOS are longer than the brilliant green molecular dye in water due to steric hindrance of the torsional degrees of freedom of the phenyl rings around the central carbon. Furthermore, the second harmonic generation signal of [BG][BETI] nanoGUMBOS is enhanced by approximately 7 times and 23 times as compared with colloidal gold nanoparticles of the same size and the brilliant green molecular dye in water, respectively. A very clear third harmonic generation signal is observed from the [BG][BETI] nanoGUMBOS but not from either the molecular dye or the gold nanoparticles. Overall, these results show that [BG][BETI] nanoGUMBOS exhibit altered ultrafast and nonlinear spectroscopy that is beneficial for various applications including nonlinear imaging probes, biomedical imaging, and molecular sensing.

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Section: Introductionmentioning

confidence: 99%

Ultrafast and nonlinear spectroscopy of brilliant green-based nanoGUMBOS with enhanced near-infrared emission

Karam

Siraj

Zhang

et al. 2017

The Journal of Chemical Physics

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“…Compound Ia represents the key-point of the implemented approach. Ia was prepared with good yield (76%) via Suzuki cross coupling between commercially available reagent 1 and 5-bromothieno[3,2- b ]thiophene-2-carbaldehyde, adapting standard protocols reported in literature for similar 2,2’ bithiophene compounds [16]. A first attempt of direct bromination of Ia in order to get IIa was done by using 2.1 eq of NBS and a similar protocol as in our previous work [15].…”

Section: Resultsmentioning

confidence: 99%

“…Recently, we have shown that “push-pull” dipolar chromophores (D-π-A), built from a bis -thiophene π-conjugated system and having a triphenylamine donor (D) moiety could indeed lead to FONs showing improved colloidal stability as a result of the replacement of a single thiophene by a bis -thiophene unit [15,16]. Following this route, we herein investigate the effect of replacing the bis -thiophene π-conjugated system by a fused analogue, i.e., the thieno[3,2- b ]thiophene moiety.…”

Section: Introductionmentioning

confidence: 99%

Molecular-Based Fluorescent Nanoparticles Built from Dedicated Dipolar Thienothiophene Dyes as Ultra-Bright Green to NIR Nanoemitters

et al. 2016

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Fluorescent Organic Nanoparticles (FONs), prepared by self-aggregation of dedicated dyes in water, represent a promising green alternative to the toxic quantum dots (QDs) for bioimaging purposes. In the present paper, we describe the synthesis and photophysical properties of new dipolar push-pull derivatives built from thieno[3,2-b]thiophene as a π-conjugated bridge that connects a triphenylamine moiety bearing various bulky substituents as electron-releasing moiety to acceptor end-groups of increasing strength (i.e., aldehyde, dicyanovinyl and diethylthiobarbiturate). All dyes display fluorescence properties in chloroform, which shifts from the green to the NIR range depending on the molecular polarization (i.e., strength of the end-groups) as well as a large two-photon absorption (TPA) band response in the biological spectral window (700-1000 nm). The TPA bands show a bathochromic shift and hyperchromic effect with increasing polarization of the dyes with maximum TPA cross-section reaching 2000 GM for small size chromophore. All dyes are found to form stable and deeply colored nanoparticles (20-45 nm in diameter) upon nanoprecipitation in water. Although their fluorescence is strongly reduced upon aggregation, all nanoparticles show large one-photon (up to 10 8 M −1 ·cm −1 in the visible region) and two-photon (up to 10 6 GM in the NIR) brightness. Interestingly, both linear and non-linear optical properties are significantly affected by interchromophoric interactions, which are promoted by the molecular confinement and modulated by both the dipolar strength and the presence of the bulky groups. Finally, we exploited the photophysical properties of the FONs to design optimized core-shell nanoparticles built from a pair of complementary dipolar dyes that promotes an efficient core-to-shell FRET process. The resulting molecular-based core-shell nanoparticles combine large two-photon absorption and enhanced emission both located in the NIR spectral region, thanks to a major amplification (by a factor of 20) of the core fluorescence quantum yield. These novel nanoparticles, which combine huge one-and two-photon brightness, hold major promise for in vivo optical bioimaging.

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“…3,11 The absorption and fluorescence spectra of all the nanoparticles have been monitored during 11 weeks: while no significant variation of the absorption spectra is observed, a decrease of the emission spectra is detected. The relatively good colloidal stability appears to be further improved by polymer doping.…”

Section: Discussionmentioning

confidence: 99%

Amplified two-photon brightness in organic multicomponent nanoparticles

et al. 2015

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In this paper we show how to easily obtain multicomponent fluorescent organic nanoparticles displaying an excitation energy-transfer cascade between the different molecular components. The use of an optically neutral polymer as dopant helps to increase the colloidal stability of the water suspensions and to slow down luminescence loss over time. In particular, core@shell@shell ternary nanoparticles are designed and investigated, providing a strongly increased luminescence in the red spectral region. The two-photon brightness of the ternary nanoparticles is greatly enhanced with respect to that of the single-component nanoparticles. In addition, these ternary nanoparticles can be two-photon excited over a broad spectral range (from 600 to 1200 nm) inside the biological transparency window. This property, together with the good colloidal stability in water suspension, suggests these fully organic multicomponent nanosystems to be very promising nanoprobes for bioimaging applications.

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A new route towards fluorescent organic nanoparticles with red-shifted emission and increased colloidal stability

Cited by 32 publications

References 35 publications

Ultrafast and nonlinear spectroscopy of brilliant green-based nanoGUMBOS with enhanced near-infrared emission

Ultrafast and nonlinear spectroscopy of brilliant green-based nanoGUMBOS with enhanced near-infrared emission

Molecular-Based Fluorescent Nanoparticles Built from Dedicated Dipolar Thienothiophene Dyes as Ultra-Bright Green to NIR Nanoemitters

Amplified two-photon brightness in organic multicomponent nanoparticles

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