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Photoswitch

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A photoswitch is a type of molecule that can change its structural geometry and chemical properties upon irradiation with electromagnetic radiation. Although often used interchangeably with the term molecular machine, a switch does not perform work upon a change in its conformation whereas a machine does.[1] However, photochromic compounds are the necessary building blocks for light driven molecular motors and machines.[2] Upon irradiation with light, photoisomerization about double bonds in the molecule can lead to changes in the cis- or trans- state.[3] These photochromic molecules have a wide range of applications across biology, chemistry, and physics.

Chemical Photoswitch

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Photoswitchable Molecules: Azobenzene undergoes a E to Z photoisomerization in which the Z isomer is more polar, has shorter bonds, and a bent and twisted geometry.[4] Hydrazone undergoes photoisomerization with long thermal half lives of thousands of years.[5] Spiropyran and Merocyanine undergo ring opening/closing mechanisms upon photo irradiation. Diarylethene and DASA exhibit changes in color upon photoisomerization. Stilbene is a model photoswitch for studying photochemistry.
Photoswitchable Molecules: Upon irradiation with light, photoisomerization occurs changing the spatial geometry and properties of the molecule.

A photochromic compound can change its conformation upon irradiation with light and includes the following as examples: azobenzene[6], spiropyran[7], merocyanine[8], diarylethene[9], spirooxazine[10], fulgide[11], hydrazone[12], nobormadiene[13], thioindigo[14], Acrylamide-Azobenzene-Quaternary Ammonia (AAQ)[15], Donor-Acceptor Stenhouse Adducts (DASA)[16], stilbene[17] etc.

Isomerization

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Upon isomerization from the absorption of light, a π to π* or n to π* electronic transition can occur with the subsequent release of light (fluorescence or phosphorescence) or heat when electrons transition from an excited state to a ground state. A photostationary state can be achieved when the irradiation of light no longer converts one form of an isomer into another; however, a mixture of cis- and trans- isomers will always exist with a higher percentage of one versus the other depending on the photoconditions.[18]

Mechanism

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Although the mechanism for photoisomerization is still debated amongst most scientists, the increasing evidence supports cis-/trans- isomerization of polyenes favoring the Hula Twist (HT) rather than the One-Bond-Flip (OBF).[19] The OBF isomerizes at

the reactive double bond while the HT undergoes a conformational isomerization at the adjacent single bond. However, the interconversion of stereoisomers of stilbene proceeds via OBF.[20]

Photoisomerization from A to B: The three rates completely describe the isomerization from A to B where where ϕA is the quantum yield, I is the photon flux, β is the fraction of photons absorbed by A, NA is Avogadro’s number, V is the volume of the sample.[21]

Quantum Yield

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One of the most important properties of a photoswitch is the quantum yield which measures how well light is absorbed to induce photoisomerization and is modeled and calculated using Arrhenius kinetics.[22] Photoswitches can be in solution or in the solid state; however, switching in the solid state is more difficult to observe due to the lack of molecular freedom of motion, solid packing, and the fast thermal reversion to the ground state.[23] Through chemical modification, red shifting the wavelengths of absorption needed to cause isomerizaiton leads to low light induced switching which has applications in the field of photopharmacology.[24]

Catalysis

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When a photochromic compound is incorporated into a suitable catalytic molecule, photoswitchable catalysis can result from the reversible changes in geometric conformation upon irradiation with light. Among the most widely studied photoswitches, azobenzene has been studied as an effective switch for regulating catalytic activity due to its isomerization from the E to Z conformation with light, and its ability to thermally relax back to the E isomer in dark conditions.[25]

Biological Photoswitch

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Retinal Photoswitch: The absorption of a photon converting cis-retinal to trans-retinal. Once converted, the trans-retinal can disassociate from Opsin. Once converted back to the cis- isomer, it can reform Rhodopsin.[26]

One of the more prevalent biological examples in the human body that are responsible to changes from light irradiation include the class of membrane-bound photoreceptors, Rhodopsins.[27] These include the regulation of melanocytes, vision, the release of melatonin and the control of the circadian rhythm, etc.[28] Rhodopsins are highly efficient photochromic compounds that can undergo fast photoisomerization and are associated with various retinal proteins[29] along with light-gated channels and pumps in microbes.[30]

Advances in vision restoration by studying natural photochromic compounds has shown promise in the last ten years. The fast isomerization is what allows retinal cells to turn on when activated by light and recent advances in AAQ have shown restoration of visual responses in blind mice.[15] Companies like Novartis, Vedere, Allergan, Nanoscope Therapeutics, etc. have been advancing the field of optogenetics and have recently entered clinical trials for vision restoration by using various forms of gene therapy and insertion of opsin based derivative molecules into damaged cells.[31]

Biological Applications

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Through the incorporation of photoswitches into biological molecules, biological processes can be regulated and controlled by the irradiation with light. This includes photocontrol of peptide conformation and activity, transcription and translation of DNA and RNA, regulation of enzymatic activity, and photoregulated ion channels.[32] For example, optical control of ligand binding in human serum albumin has been demonstrated and can influence the allosteric binding properties.[33] Also, red-shifted azobenzenes have been used to control ionotropic glutamate receptors.[34]

Applications

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Photoswitches are utilized by many disciplines of science that include biology, materials chemistry, and physics and have a wide variety of applications that are crucial to the framework of nanotechnology.[35]

Electronics

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Depending on the isomeric state, photoswitches can be turned on and off and have the potential to one day replace transistors used in electronics.[36] Through the attachment of photoswitches onto the surfaces of different substrates, the work function can be changed. For example, the incorporation of diarylethenes as a self-assembled monolayer on a gold surface shows promise in optoelectronic devices.[37]

Diarylethenes have been shown to form stable molecular conduction junctions when placed between graphene electrodes at low and room temperature and act as a photo-electrical switch.[38] By combining a photoswitch, containing different HOMO and LUMO levels in its open and closed geometrical conformation, into a film composed of either p- or n-doped semiconductors, charge transport can be controlled with light.[37] A photo-electric cell is connected to a circuit that measures how much electricity the cell produces and according to the setting of minimum and maximum lux level, the circuit decides and gives the output.[39]

Photoswitches have recently also been used in the generation of three-dimensional animations and images.[40]The display utilizes a medium composed of a class of photoswitches (known as spirhodamines) and digital light processing (DLP) technology to generate structured light in three dimensions. UV light and green light patterns are aimed at the dye solution, which initiates photoactivation and thus creates the 'on' voxel. The device is capable of displaying a minimum voxel size of 0.68 mm^3, with 200 μm resolution, and good stability over hundreds of on-off cycles.

Energy Storage

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Due to one of the photoisomers being more stable than the other, isomerization from the stable to metastable isomer results in a conversion of light energy into free energy as a form of a chemical potential and has applications in storing solar energy.[41]

Mercocyanine has been shown to shuttle protons across a polymeric membrane upon irradiation with light. When UV and visible light were irradiated upon opposites sides of the membrane generated a storage potential as well as a pH gradient.[37]

Guest Uptake and Release

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Incorporation of photoswitchable molecules in porous metal organic frameworks can be used for the uptake of gaseous molecules like carbon dioxide as well as contribute to optoelectronics, nanomedicine, and better energy storage. By changing the chemical properties of the pores, adsorption and desorption of gases can be tuned for advancements in smart membrane materials.[37]

Liquid Crystals

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Chiral shape driven transformations in liquid crystal structures can be achieved through photoisomerization of bistable hydrazones to generate long term stable polymer shapes.[42] Light gated optical windows that can change the absorbance properties can be made through the chiral doping of liquid crystals with hydrazone photoswitches, kinetically trapping various cholesteric states as a function of the photostationary state.[43] Incorporation of photoswitches into nematic liquid crystals can change self-assembly, crystal packing, and the light reflecting properties of the supramolecular interactions.[44]

Optical Storage

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Diarylethene photoswitches have been promising for use in rewritable optical storage. Through irradiation of light, writing, erasing, and reading can parallel CD/DVD storage with better performance.[45]

Photopharmacology

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In the field of photopharmacology, photoswitches are used to obtain control over the activity. By including a photoswitch to the drugs, a drug with several states is created, all having their own biological activity. Light can be used to switch between these states, resulting in drugs with remote control over the activity.[46] Photoswiches have been shown to be able to change the surface energy properties of nanoparticles which can control how the photoswitchable shell interacts with nanoparticles.[47] Pharmaceutical encapsulation and distribution at targeted locations with light has been demonstrated due to the unique change in properties and size of microencapsulated nanostructures with photochromic components.[48]

Self-Healing Materials

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Two strategies have been incorporated to utilize photoswitches for self-healable polymer materials. The first incorporates the phototunability of various functional groups so reactivity can be modulated in one of the isomeric forms, while the second strategy incorporates light-driven valence bond tautomerization.[37]

References

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  1. ^ Aprahamian, Ivan (2020-03-25). "The Future of Molecular Machines". ACS Central Science. 6 (3): 347–358. doi:10.1021/acscentsci.0c00064. ISSN 2374-7943. PMC 7099591. PMID 32232135.{{cite journal}}: CS1 maint: PMC format (link)
  2. ^ Kassem, Salma; Leeuwen, Thomas van; Lubbe, Anouk S.; Wilson, Miriam R.; Feringa, Ben L.; Leigh, David A. (2017-05-09). "Artificial molecular motors". Chemical Society Reviews. 46 (9): 2592–2621. doi:10.1039/C7CS00245A. ISSN 1460-4744.
  3. ^ Cameron, David; Eisler, Sara (2018). "Photoswitchable double bonds: Synthetic strategies for tunability and versatility". Journal of Physical Organic Chemistry. 31 (10): e3858. doi:10.1002/poc.3858. ISSN 1099-1395.
  4. ^ Goulet‐Hanssens, Alexis; Eisenreich, Fabian; Hecht, Stefan (2020). "Enlightening Materials with Photoswitches". Advanced Materials. 32 (20): 1905966. doi:10.1002/adma.201905966. ISSN 1521-4095.
  5. ^ Qian, Hai; Pramanik, Susnata; Aprahamian, Ivan (2017-07-12). "Photochromic Hydrazone Switches with Extremely Long Thermal Half-Lives". Journal of the American Chemical Society. 139 (27): 9140–9143. doi:10.1021/jacs.7b04993. ISSN 0002-7863.
  6. ^ Bandara, H. M. Dhammika; Burdette, Shawn C. (2012-02-13). "Photoisomerization in different classes of azobenzene". Chemical Society Reviews. 41 (5): 1809–1825. doi:10.1039/C1CS15179G. ISSN 1460-4744.
  7. ^ Kortekaas, Luuk; Browne, Wesley R. (2019-06-17). "The evolution of spiropyran: fundamentals and progress of an extraordinarily versatile photochrome". Chemical Society Reviews. 48 (12): 3406–3424. doi:10.1039/C9CS00203K. ISSN 1460-4744.
  8. ^ Klajn, Rafal (2014). "Spiropyran-based dynamic materials". Chemical Society Reviews. 43 (1): 148–184. doi:10.1039/C3CS60181A.
  9. ^ Pu, Shou-Zhi; Sun, Qi; Fan, Cong-Bin; Wang, Ren-Jie; Liu, Gang (2016-04-14). "Recent advances in diarylethene-based multi-responsive molecular switches". Journal of Materials Chemistry C. 4 (15): 3075–3093. doi:10.1039/C6TC00110F. ISSN 2050-7534.
  10. ^ Berkovic, Garry; Krongauz, Valeri; Weiss, Victor (2000-05-01). "Spiropyrans and Spirooxazines for Memories and Switches". Chemical Reviews. 100 (5): 1741–1754. doi:10.1021/cr9800715. ISSN 0009-2665.
  11. ^ Yokoyama, Yasushi (2000-05-01). "Fulgides for Memories and Switches". Chemical Reviews. 100 (5): 1717–1740. doi:10.1021/cr980070c. ISSN 0009-2665.
  12. ^ Su, Xin; Aprahamian, Ivan (2014-02-24). "Hydrazone-based switches, metallo-assemblies and sensors". Chemical Society Reviews. 43 (6): 1963–1981. doi:10.1039/C3CS60385G. ISSN 1460-4744.
  13. ^ Orrego-Hernández, Jessica; Dreos, Ambra; Moth-Poulsen, Kasper (2020-08-18). "Engineering of Norbornadiene/Quadricyclane Photoswitches for Molecular Solar Thermal Energy Storage Applications". Accounts of Chemical Research. 53 (8): 1478–1487. doi:10.1021/acs.accounts.0c00235. ISSN 0001-4842. PMC 7467572. PMID 32662627.{{cite journal}}: CS1 maint: PMC format (link)
  14. ^ Navrátil, Rafael; Wiedbrauk, Sandra; Jašík, Juraj; Dube, Henry; Roithová, Jana (2018-03-07). "Transforming hemithioindigo from a two-way to a one-way molecular photoswitch by isolation in the gas phase". Physical Chemistry Chemical Physics. 20 (10): 6868–6876. doi:10.1039/C8CP00096D. ISSN 1463-9084.
  15. ^ a b Polosukhina, Aleksandra; Litt, Jeffrey; Tochitsky, Ivan; Nemargut, Joseph; Sychev, Yivgeny; DeKouchkovsky, Ivan; Huang, Tracy; Borges, Katharine; Trauner, Dirk; VanGelder, Russell N.; Kramer, Richard H. (2012-07-26). "Photochemical Restoration of Visual Responses in Blind Mice". Neuron. 75 (2): 271–282. doi:10.1016/j.neuron.2012.05.022. ISSN 0896-6273. PMID 22841312.
  16. ^ Lerch, Michael M.; Szymański, Wiktor; Feringa, Ben L. (2018-03-19). "The (photo)chemistry of Stenhouse photoswitches: guiding principles and system design". Chemical Society Reviews. 47 (6): 1910–1937. doi:10.1039/C7CS00772H. ISSN 1460-4744.
  17. ^ Abourashed, Ehab A. (2017-02-24). "Review of Stilbenes: Applications in Chemistry, Life Sciences and Materials Science". Journal of Natural Products. 80 (2): 577–577. doi:10.1021/acs.jnatprod.7b00089. ISSN 0163-3864.
  18. ^ Roberts, John D.; Caserio, Marjorie C. (1977-05-15). Basic Principles of Organic Chemistry, second edition. Menlo Park, CA: W. A. Benjamin, Inc. ISBN 978-0-8053-8329-4.
  19. ^ Liu, Robert S. H. (2001-07-01). "Photoisomerization by Hula-Twist:  A Fundamental Supramolecular Photochemical Reaction". Accounts of Chemical Research. 34 (7): 555–562. doi:10.1021/ar000165c. ISSN 0001-4842.
  20. ^ Liu, Robert S. H.; Hammond, George S. (2000-10-10). "The case of medium-dependent dual mechanisms for photoisomerization: One-bond-flip and Hula-Twist". Proceedings of the National Academy of Sciences. 97 (21): 11153–11158. doi:10.1073/pnas.210323197. ISSN 0027-8424. PMID 11016972.
  21. ^ Stranius, K.; Börjesson, K. (2017-01-24). "Determining the Photoisomerization Quantum Yield of Photoswitchable Molecules in Solution and in the Solid State". Scientific Reports. 7 (1): 41145. doi:10.1038/srep41145. ISSN 2045-2322.
  22. ^ Stranius, K.; Börjesson, K. (2017-01-24). "Determining the Photoisomerization Quantum Yield of Photoswitchable Molecules in Solution and in the Solid State". Scientific Reports. 7 (1): 41145. doi:10.1038/srep41145. ISSN 2045-2322.
  23. ^ "Solid-state photoswitching molecules: structural design for isomerization in condensed phase". Materials Today Advances. 6: 100058. 2020-06-01. doi:10.1016/j.mtadv.2020.100058. ISSN 2590-0498.
  24. ^ Wegner, Hermann A. (2012). "Azobenzenes in a New Light—Switching In Vivo". Angewandte Chemie International Edition. 51 (20): 4787–4788. doi:10.1002/anie.201201336. ISSN 1521-3773.
  25. ^ Dorel, Ruth; Feringa, Ben L. (2019-06-04). "Photoswitchable catalysis based on the isomerisation of double bonds". Chemical Communications. 55 (46): 6477–6486. doi:10.1039/C9CC01891C. ISSN 1364-548X.
  26. ^ "Photochemical Changes in Opsin". Chemistry LibreTexts. 2013-10-02. Retrieved 2021-02-24.
  27. ^ Ernst, Oliver P.; Lodowski, David T.; Elstner, Marcus; Hegemann, Peter; Brown, Leonid S.; Kandori, Hideki (2014-01-08). "Microbial and Animal Rhodopsins: Structures, Functions, and Molecular Mechanisms". Chemical Reviews. 114 (1): 126–163. doi:10.1021/cr4003769. ISSN 0009-2665. PMC 3979449. PMID 24364740.{{cite journal}}: CS1 maint: PMC format (link)
  28. ^ "Photochemical reaction | chemical reaction". Encyclopedia Britannica.{{cite web}}: CS1 maint: url-status (link)
  29. ^ Inuzuka, Kozo; Becker, Ralph S. (1968-07). "Mechanism of Photoisomerization in the Retinals and Implications in Rhodopsin". Nature. 219 (5152): 383–385. doi:10.1038/219383a0. ISSN 1476-4687. {{cite journal}}: Check date values in: |date= (help)
  30. ^ Kandori, Hideki (2020-02-17). "Biophysics of rhodopsins and optogenetics". Biophysical Reviews. 12 (2): 355–361. doi:10.1007/s12551-020-00645-0. ISSN 1867-2450. PMC 7242518. PMID 32065378.
  31. ^ Ratner, Mark (2021-02-01). "Light-activated genetic therapy to treat blindness enters clinic". Nature Biotechnology. 39 (2): 126–127. doi:10.1038/s41587-021-00823-9. ISSN 1546-1696.
  32. ^ Szymański, Wiktor; Beierle, John M.; Kistemaker, Hans A. V.; Velema, Willem A.; Feringa, Ben L. (2013-08-14). "Reversible Photocontrol of Biological Systems by the Incorporation of Molecular Photoswitches". Chemical Reviews. 113 (8): 6114–6178. doi:10.1021/cr300179f. ISSN 0009-2665.
  33. ^ Putri, Rindia M.; Zulfikri, Habiburrahman; Fredy, Jean Wilfried; Juan, Alberto; Tananchayakul, Pichayut; Cornelissen, Jeroen J. L. M.; Koay, Melissa S. T.; Filippi, Claudia; Katsonis, Nathalie (2018-07-18). "Photoprogramming Allostery in Human Serum Albumin". Bioconjugate Chemistry. 29 (7): 2215–2224. doi:10.1021/acs.bioconjchem.8b00184. ISSN 1043-1802. PMC 6053643. PMID 29975051.{{cite journal}}: CS1 maint: PMC format (link)
  34. ^ Kienzler, Michael A.; Reiner, Andreas; Trautman, Eric; Yoo, Stan; Trauner, Dirk; Isacoff, Ehud Y. (2013-11-27). "A Red-Shifted, Fast-Relaxing Azobenzene Photoswitch for Visible Light Control of an Ionotropic Glutamate Receptor". Journal of the American Chemical Society. 135 (47): 17683–17686. doi:10.1021/ja408104w. ISSN 0002-7863. PMC 3990231. PMID 24171511.{{cite journal}}: CS1 maint: PMC format (link)
  35. ^ Sinicropi, Adalgisa. "Biomimetic Photoswitches". Inorganica Chimica Acta. 470: 360–364. doi:10.1016/j.ica.2017.08.041. ISSN 0020-1693.
  36. ^ "The future of electronics is photoswitches". BrandeisNOW.{{cite web}}: CS1 maint: url-status (link)
  37. ^ a b c d e Goulet‐Hanssens, Alexis; Eisenreich, Fabian; Hecht, Stefan (2020). "Enlightening Materials with Photoswitches". Advanced Materials. 32 (20): 1905966. doi:10.1002/adma.201905966. ISSN 1521-4095.
  38. ^ Jia, Chuancheng; Migliore, Agostino; Xin, Na; Huang, Shaoyun; Wang, Jinying; Yang, Qi; Wang, Shuopei; Chen, Hongliang; Wang, Duoming; Feng, Boyong; Liu, Zhirong (2016-06-17). "Covalently bonded single-molecule junctions with stable and reversible photoswitched conductivity". Science. 352 (6292): 1443–1445. doi:10.1126/science.aaf6298. ISSN 0036-8075. PMID 27313042.
  39. ^ "How do photoelectric cells work?". Explain that Stuff.{{cite web}}: CS1 maint: url-status (link)
  40. ^ Patel, Shreya K.; Cao, Jian; Lippert, Alexander R. (2017-07-11). "A volumetric three-dimensional digital light photoactivatable dye display". Nature Communications. 8. doi:10.1038/ncomms15239. ISSN 2041-1723. PMC 5508202. PMID 28695887.
  41. ^ Sun, Cai-Li; Wang, Chenxu; Boulatov, Roman (2019). "Applications of Photoswitches in the Storage of Solar Energy". ChemPhotoChem. 3 (6): 268–283. doi:10.1002/cptc.201900030. ISSN 2367-0932.
  42. ^ Ryabchun, Alexander; Li, Quan; Lancia, Federico; Aprahamian, Ivan; Katsonis, Nathalie (2019-01-23). "Shape-Persistent Actuators from Hydrazone Photoswitches". Journal of the American Chemical Society. 141 (3): 1196–1200. doi:10.1021/jacs.8b11558. ISSN 0002-7863. PMC 6346373. PMID 30624915.{{cite journal}}: CS1 maint: PMC format (link)
  43. ^ Moran, Mark J.; Magrini, Mitchell; Walba, David M.; Aprahamian, Ivan (2018-10-24). "Driving a Liquid Crystal Phase Transition Using a Photochromic Hydrazone". Journal of the American Chemical Society. 140 (42): 13623–13627. doi:10.1021/jacs.8b09622. ISSN 0002-7863.
  44. ^ Zhang, Xinfang; Koz, Banu; Bisoyi, Hari Krishna; Wang, Hao; Gutierrez-Cuevas, Karla G.; McConney, Michael E.; Bunning, Timothy J.; Li, Quan (2020-12-09). "Electro- and Photo-Driven Orthogonal Switching of a Helical Superstructure Enabled by an Axially Chiral Molecular Switch". ACS Applied Materials & Interfaces. 12 (49): 55215–55222. doi:10.1021/acsami.0c19527. ISSN 1944-8244.
  45. ^ Rosenbaum, Lisa-Catherine (November 7, 2018). "Organic Photochromic Compounds" (PDF). Universitat Konstanz.{{cite web}}: CS1 maint: url-status (link)
  46. ^ Velema, Willem A.; Szymanski, Wiktor; Feringa, Ben L. (2014-02-12). "Photopharmacology: Beyond Proof of Principle". Journal of the American Chemical Society. 136 (6): 2178–2191. doi:10.1021/ja413063e. ISSN 0002-7863.
  47. ^ Velema, Willem A.; Szymanski, Wiktor; Feringa, Ben L. (2014-02-12). "Photopharmacology: Beyond Proof of Principle". Journal of the American Chemical Society. 136 (6): 2178–2191. doi:10.1021/ja413063e. ISSN 0002-7863.
  48. ^ Guo, Xing; Shao, Baihao; Zhou, Shaobing; Aprahamian, Ivan; Chen, Zi (2020-03-18). "Visualizing intracellular particles and precise control of drug release using an emissive hydrazone photochrome". Chemical Science. 11 (11): 3016–3021. doi:10.1039/C9SC05321B. ISSN 2041-6539.
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