Fluorescent Photoswitchable Systems

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Abstract

Fluorescent photoswitchable systems (FPSS) are organic molecular and organic-inorganic hybrid nanoscale systems that combine the properties of photochromes and fluorophores, i.e. the ability to change their fluorescent properties, intensity and/or emission spectrum under the action of light. The structure and mechanisms of action of FPSS of different types are considered, examples of application of FPSS in super-resolution microscopy, for visualisation of biological and inorganic nano-objects, recording of optical information, for anti-counterfeiting, as photonic molecular logic gates are given.

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About the authors

М. F. Budyka

Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry of the Russian Academy of Sciences

Author for correspondence.
Email: budyka@icp.ac.ru
Russian Federation, Chernogolovka

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Supplementary files

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1. JATS XML
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2. Fig. 1. General scheme of processes in the lowest singlet-excited state of the molecule (see text for notations).

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3. Fig. 2. Photoisomerisation of spiropyran into merocyanine.

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4. Fig. 3. Use of 70 nm nanoparticles to compare conventional fluorescence microscopy (top) and MSWR (bottom). The PULSAR microscope improves resolution by a factor of about 25, effectively distinguishing features at the nanoscale [35].

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5. Fig. 4. Photocyclisation of diarylethene to dihydrophenanthrene derivative.

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6. Scheme 1

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7. Scheme 2

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8. Scheme 3

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9. Fig. 5. Photoisomerisation of diarylethenes between trans and cis isomers.

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10. Fig. 6. Photochemical reactions in bis-styrylquinoline dyad 4.

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11. Fig. 7. The photochemical transformation cycle of the bichromophoric dyad (left) and the cycle of transitions between states of the bi-channel logic valve (right).

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12. Fig. 8. Change of luminescence intensity of dyad 4 at 440 nm as a response to external influence: initial state - photostationary state of PS365, input signals (in1 = in2) - irradiation with 313 nm light, return to initial state (reset) - irradiation with 365 nm light. Horizontal dashed lines show the threshold values of optical densities for analogue to digital signal conversion for OR and AND valves [57].

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13. Fig. 9. The [2+2]-photocycloaddition reaction in the EE-isomer of dyad 5 to form tetrasubstituted cyclobutane 6.

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14. Fig. 10. Fluorescence spectra (excitation at 352 nm): cyclobutane 6 (1), the same sample after irradiation with light at λ = 316 nm for 3000 s (2); fluorescence excitation spectra: cyclobutane 6 (3, observation at 380 nm), after irradiation with light at λ = 316 nm for 3000 s (4, observation at 465 nm, spectrum reduced by a factor of 2). Inset: variation of the fluorescence intensity of the sample (excitation at 352 nm) at wavelengths: 380 (5) and 465 nm (6) upon alternate irradiation with light with λ = 316 nm for 3000 s and λ = 442 nm for 500 s [65].

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15. Fig. 11. Photodissociation of aromatic azides to form amines.

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16. Fig. 12. Schematic of the operation of two-component FFPS by the electron transfer (ET) mechanism: F - fluorophore, S - spacer, P - photochromium; HOMO and LUMO - highest occupied and lowest vacant molecular orbitals; A and B - isomers of photochromium.

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17. Scheme 4

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18. Fig. 13. Scheme of operation of two-component FFPS by the energy transfer (ET) mechanism: F - fluorophore, S - spacer, P - photochromium; S0 and S1 - energy levels of ground and lowest singlet-excited states; A and B - isomers of photochromium.

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19. Scheme 5

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20. Scheme 6

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21. Fig. 14. Absorption (1) and fluorescence (2, λexc = 339 nm) spectra of dyad 9 [91].

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22. Scheme 7

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23. Scheme 8

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24. Fig. 15. Schematic structure of a hybrid organo-inorganic PFPS containing a QCT (QD), a stabilising (coating) ligand (L) and a photochromic functional ligand (PL).

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25. Fig. 16. Variation of the emission intensity of KKT (QD) at 550 nm (excitation at 400 nm) and Alexa647 dye at 666 nm (excitation at 600 nm) upon alternate irradiation of hybrid PFPS with light with λ = 340 and 545 nm [115].

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26. Fig. 17. Normalised spectra: fluorescence of KKT (1, excitation at 370 nm), absorption of trans-isomer (2) and cis-isomer (3) of AQE-ligand. The inset shows the change in the emission intensity of KKT (4) and AQE-ligand (5) under alternate irradiation of hybrid PFPS with light with λ = 370 and 462 nm; excitation at 414 nm, observation at 417 nm (KKT) and 520 nm (AQE); according to [116].

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27. Scheme 9

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