Stealth Luminescent Organic Nanoparticles Made from Quadrupolar Dyes for Two-Photon Bioimaging: Effect of End-Groups and Core
Abstract
:1. Introduction
2. Results and Discussion
2.1. Design
2.2. Synthesis of the Dyes
2.3. Photophysical Properties of the Quadrupolar Dyes in Solution
2.3.1. Absorption
2.3.2. Fluorescence
2.3.3. Two-Photon Absorption Properties
2.4. Preparation and Characterisation of the FONs
2.4.1. Nanoprecipitation
2.4.2. Optical Properties of FONs
2.5. Bioimaging: Usability and Interactions with Cells
3. Materials and Methods
3.1. Chemical Characterisations
3.2. Quantum Chemical Calculations
3.3. Dye Synthesis
3.3.1. Synthesis of Q1
3.3.2. Synthesis of Q2
3.3.3. Synthesis of Q3
3.3.4. Synthesis of Q4
3.4. Spectroscopy
3.4.1. One-Photon Spectroscopy
3.4.2. Two-Photon Excited Fluorescence Spectroscopy
3.4.3. Lifetime Measurements
3.5. Zeta Potential Measurements
3.6. FONs Preparation
3.7. Transmission Electron Microscopy
3.8. Cell Culture and Bioimaging
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Dye /Solvent | λ1PAmax [nm] (a) | εmax [M−1.cm−1] (b) | FWHM [103 cm−1] (c) | λemmax [nm] (d) | Φf (e) | Stokes Shift [103 cm−1] | τ [ns] (f) | kr [108 s−1] (g) | knr [108 s−1] (h) | SSS [cm−1] (i) | 2λ1PAmax [nm] | λ2PAmax [nm] (j) | σ2max [GM] (k) |
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Q1/Tol | 462 348 | 4.5 × 104 5.5 × 104 | 3.6 | 548 | 0.82 | 3.4 | 2.3 | 3.6 | 0.8 | 17.4 × 103 | 924 696 | 910 820 750 | 130 1100 760 |
Q1/THF | 461 347 | 5.2 × 104 6.7 × 104 | 3.9 | 646 | 0.33 | 6.2 | 3.2 | 1.0 | 2.1 | - | - | - | |
Q1/FONs | 467 | 4.7 × 104 | 3.5 | 628 | 0.05 | 5.5 | 1.1 (0.26) 5.5 (0.47) 20 (0.27) | 0.06 | 1.1 | - | 934 | 880 820 750 | 430 570 300 |
Q2/Tol | 476 369 | 4.2 × 104 5.5 × 104 | 4.1 | 569 | 0.92 | 3.4 | 2.8 | 3.3 | 0.3 | 20 × 103 | 952 738 | 870 820 730 | 990 1200 400 |
Q2/THF | 474 369 | 4.2 × 104 5.7 × 104 | 4.4 | 688 | 0.14 | 6.6 | 2.2 | 0.6 | 3.9 | - | - | - | |
Q2/FONs | 480 | 3.3 × 104 | 4.4 | 623 | 0.04 | 4.8 | 1.0 (0.31) 4.5 (0.42) 17 (0.27) | 0.06 | 1.4 | - | 960 | 890 840 | 940 980 |
Q3/Tol | 495 378 | 4.3 × 104 7.0 × 104 | 3.9 | 595 | 0.80 | 3.4 | 2.0 | 3.9 | 1.1 | 22.4 × 103 | 992 | 1020 890 820 730 | 190 1050 650 320 |
Q3/THF | 493 377 | 5.1 × 104 7.5 × 104 | 4.3 | 737 | - | 6.7 | - | - | - | - | - | - | |
Q3/FONs | 503 | 4.4 × 104 | 4.5 | 688 | <0.01 | 5.3 | 1.7 (0.17) 5.9 (0.45) 15.5 (0.38) | 0.04 | 3.6 | - | 1006 | 940 890 | - * |
Q4/Tol | 484 371 | 2.9 × 104 3.6 × 104 | 4.3 | 582 | 0.44 | 3.5 | 1.2 | 3.7 | 4.5 | 20.6 × 103 | 968 | 1030 880 820 760 | 90 340 460 300 |
Q4/THF | 477 368 | 3.4 × 104 4.1 × 104 | 4.9 | 718 | 0.03 | 7.0 | 0.8 | 3.8 | 12.3 | - | - | - | |
Q4/FONs | 485 | 2.6 × 104 | 4.6 | 656 | 0.02 | 5.3 | 0.9 (0.30) 4.8 (0.40) 17.8 (0.30) | 0.14 | 4.4 | - | 970 | 900 830 | - * |
Dye | Transition | ∆Ege [eV] | λge [nm] | fge | ∆µge [D] |
---|---|---|---|---|---|
Q1 | S0→S1 | 2.794 | 444 | 2.285 | 0.763 |
S0→S2 | 3.499 | 354 | 0.188 | - | |
S0→S3 | 3.673 | 338 | 1.109 | - | |
S0→S4 | 3.875 | 320 | 0.454 | - | |
S0→S5 | 4.017 | 309 | 0.331 | - | |
Q2 | S0→S1 | 2.7541 | 450 | 2.245 | 0.457 |
S0→S2 | 3.418 | 363 | 0.081 | - | |
S0→S3 | 3.697 | 335 | 0.860 | - | |
S0→S4 | 4.004 | 310 | 0.098 | - | |
S0→S5 | 4.040 | 307 | 0.732 | - | |
Q3 | S0→S1 | 2.706 | 458 | 2.308 | 0.063 |
S0→S2 | 3.288 | 377 | 0.074 | - | |
S0→S3 | 3.608 | 344 | 0.538 | - | |
S0→S4 | 3.885 | 319 | 0.878 | - | |
S0→S5 | 3.906 | 317 | 0.329 | - | |
Q4 | S0→S1 | 2.682 | 462 | 2.546 | 0.453 |
S0→S2 | 3.174 | 391 | 0.000 | - | |
S0→S3 | 3.565 | 348 | 0.011 | - | |
S0→S4 | 3.610 | 343 | 0.680 | - | |
S0→S5 | 3.901 | 318 | 0.009 | - |
Dye | dTEM (a) [nm] | ζ-pot (b) [mV] | N (c) | λabs1P,max [nm] | εmax (d) [108 M−1cm−1] | λemmax [nm] | εmax Φf (e) [106 M−1cm−1] | λabs2P,max [nm] | σ2max Φf (f) [104 GM] |
---|---|---|---|---|---|---|---|---|---|
Q1 | 13 27 | −70 | 614 5502 | 467 | 0.3 2.6 | 628 | 1.5 13.6 | 790 | 2.2 19.5 |
Q2 | 12 | −67 | 509 | 480 | 0.2 | 623 | 0.7 | 890 | 2.1 |
Q3 | 11 28 | −42 | 352 5806 | 503 | 0.2 2.6 | 686 | 0.1 2.1 | 890 | 0.4 6.5 |
Q4 | 19 | −66 | 1793 | 485 | 0.5 | 656 | 1.0 | 900 | 4.7 |
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Rosendale, M.; Daniel, J.; Castet, F.; Pagano, P.; Verlhac, J.-B.; Blanchard-Desce, M. Stealth Luminescent Organic Nanoparticles Made from Quadrupolar Dyes for Two-Photon Bioimaging: Effect of End-Groups and Core. Molecules 2022, 27, 2230. https://doi.org/10.3390/molecules27072230
Rosendale M, Daniel J, Castet F, Pagano P, Verlhac J-B, Blanchard-Desce M. Stealth Luminescent Organic Nanoparticles Made from Quadrupolar Dyes for Two-Photon Bioimaging: Effect of End-Groups and Core. Molecules. 2022; 27(7):2230. https://doi.org/10.3390/molecules27072230
Chicago/Turabian StyleRosendale, Morgane, Jonathan Daniel, Frédéric Castet, Paolo Pagano, Jean-Baptiste Verlhac, and Mireille Blanchard-Desce. 2022. "Stealth Luminescent Organic Nanoparticles Made from Quadrupolar Dyes for Two-Photon Bioimaging: Effect of End-Groups and Core" Molecules 27, no. 7: 2230. https://doi.org/10.3390/molecules27072230