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146:. Triplet states typically have longer lifetimes than excited singlets. The prolonged lifetime increases the probability of interacting with other molecules nearby. Photosensitizers experience varying levels of efficiency for intersystem crossing at different wavelengths of light based on the internal electronic structure of the molecule.
252:
molecules, which could facilitate synthetic chemistry reactions. However, by the 1970s and 1980s, photosensitizers gained attraction in the scientific community for their role within biologic processes and enzymatic processes. Currently, photosensitizers are studied for their contributions to fields
247:
The term photosensitizer does not appear in scientific literature until the 1960s. Instead, scientists would refer to photosensitizers as sensitizers used in photo-oxidation or photo-oxygenation processes. Studies during this time period involving photosensitizers utilized organic photosensitizers,
226:
and other light sensitive molecules have been a part of plant life, but studies of photosensitizers began as early as the 1900s, where scientists observed photosensitization in biological substrates and in the treatment of cancer. Mechanistic studies related to photosensitizers began with scientists
618:
reactions. Photosensitizers in synthetic chemistry allow for the manipulation of electronic transitions within molecules through an externally applied light source. These photosensitizers used in redox chemistry may be organic, organometallic, or nanomaterials depending on the physical and spectral
511:
to treat skin tumors. The photodynamic process is predominantly a noninvasive technique wherein the photosensitizers are put inside a patient so that it may accumulate on the tumor or cancer. When the photosensitizer reaches the tumor or cancer, wavelength specific light is shined on the outside of
578:
to semiconductor surfaces which allows for the transfer of light energy from the photosensitizer to electronic energy within the semiconductor. These photosensitizers are not limited to dyes. They may take the form of any photosensitizing structure, dependent on the semiconductor material to which
281:
In Type I photosensitized reactions, the photosensitizer is excited by a light source into a triplet state. The excited, triplet state photosensitizer then reacts with a substrate molecule which is not molecular oxygen to both form a product and reform the photosensitizer. Type I photosensitized
456:
materials with highly tunable optical and electronic properties. Quantum dots photosensitize via the same mechanism as organometallic photosensitizers and organic photosensitizers, but their nanoscale properties allow for greater control in distinctive aspects. Some key advantages to the use of
213:
can occur in two ways. Photopolymerization can occur directly wherein the monomers absorb the incident light and begin polymerizing, or it can occur through a photosensitizer-mediated process where the photosensitizer absorbs the light first before transferring energy into the monomer species.
627:
Photosensitizers that are readily incorporated into the external tissues can increase the rate at which reactive oxygen species are generated upon exposure to UV light (such as UV-containing sunlight). Some photosensitizing agents, such as St. John's Wort, appear to increase the incidence of
411:
Organic photosensitizers are carbon-based molecules which are capable of photosensitizing. The earliest studied photosensitizers were aromatic hydrocarbons which absorbed light in the presence of oxygen to produce reactive oxygen species. These organic photosensitizers are made up of highly
472:, similar in size to quantum dots, have tunable optical and electronic properties. Based on their size and material composition, it is possible to tune the maximum absorption peak for nanorods during their synthesis. This control has led to the creation of photosensitizing nanorods.
601:
In the early 20th century, chemists observed that various aromatic hydrocarbons in the presence of oxygen could absorb wavelength specific light to generate a peroxide species. This discovery of oxygen's reduction by a photosensitizer led to chemists studying photosensitizers as
561:
In 1972, scientists discovered that chlorophyll could absorb sunlight and transfer energy into electrochemical cells. This discovery eventually led to the use of photosensitizers as sunlight-harvesting materials in solar cells, mainly through the use of photosensitizer dyes.
516:
frequency as this allows for the penetration of the skin without acute toxicity) excites the photosensitizer's electrons into the triplet state. Upon excitation, the photosensitizer begins transferring energy to neighboring ground state triplet oxygen to generate excited
587:
Via the absorption of light, photosensitizers can utilize triplet state transfer to reduce small molecules, such as water, to generate
Hydrogen gas. As of right now, photosensitizers have generated hydrogen gas by splitting water molecules at a small, laboratory scale.
432:
allow for these materials to enter their triplet state more efficiently, making them better photosensitizers. Some notable organic photosensitizers which have been studied extensively include benzophenones, methylene blue, rose Bengal, flavins, pterins and others.
420:. Due to their high conjugation, these systems have a smaller gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) as well as a continuum of orbitals within the HOMO and LUMO. The smaller
1303:
Sang X, Li J, Zhang L, Wang Z, Chen W, Zhu Z, et al. (May 2014). "A novel carboxyethyltin functionalized sandwich-type germanotungstate: synthesis, crystal structure, photosensitivity, and application in dye-sensitized solar cells".
310:
molecule reacts with a substrate to form a product. Type II photosensitized reaction result in the photosensitizer being quenched by a ground state oxygen molecule which then goes on to react with a substrate to form a product.
1869:
Zeng W, Cao Y, Bai Y, Wang Y, Shi Y, Zhang M, et al. (2010-03-09). "Efficient Dye-Sensitized Solar Cells with an
Organic Photosensitizer Featuring Orderly Conjugated Ethylenedioxythiophene and Dithienosilole Blocks".
205:(or photobases) are molecules which become more acidic (or basic) upon the absorption of light. Photoacids increase in acidity upon absorbing light and thermally reassociate back into their original form upon relaxing.
41:. They can function by many mechanisms, sometimes they donate an electron to the substrate, sometimes they abstract a hydrogen atom from the substrate. At the end of this process, the photosensitizer returns to its
319:
Photosensitizers can be placed into 3 generalized domains based on their molecular structure. These three domains are organometallic photosensitizers, organic photosensitizers, and nanomaterial photosensitizers.
1905:
McCullough BJ, Neyhouse BJ, Schrage BR, Reed DT, Osinski AJ, Ziegler CJ, White TA (March 2018). "Visible-Light-Driven
Photosystems Using Heteroleptic Cu(I) Photosensitizers and Rh(III) Catalysts To Produce
231:
molecular oxygen into peroxide species. The results were understood by calculating quantum efficiencies and fluorescent yields at varying wavelengths of light and comparing these results with the yield of
185:. Photosensitizers utilize light to enact a chemical change in a substrate; after the chemical change, the photosensitizer returns to its initial state, remaining chemically unchanged from the process.
356:. The photosensitizing capacities of these molecules result from electronic interactions between the metal and ligand(s). Popular electron-rich metal centers for these complexes include
1639:
Jang B, Park JY, Tung CH, Kim IH, Choi Y (February 2011). "Gold nanorod-photosensitizer complex for near-infrared fluorescence imaging and photodynamic/photothermal therapy in vivo".
1440:
Zhang Y, Lee TS, Petersen JL, Milsmann C (May 2018). "A Zirconium
Photosensitizer with a Long-Lived Excited State: Mechanistic Insight into Photoinduced Single-Electron Transfer".
813:
Zhang Y, Lee TS, Petersen JL, Milsmann C (May 2018). "A Zirconium
Photosensitizer with a Long-Lived Excited State: Mechanistic Insight into Photoinduced Single-Electron Transfer".
298:
In Type II photosensitized reactions, the photosensitizer is excited by a light source into a triplet state. The excited photosensitizer then reacts with a ground state,
461:
which allows for efficient transitions to the triplet state, and their insolubility in many solvents which allows for easy retrieval from a synthetic reaction mixture.
201:
accelerate chemical reactions which rely upon light. While some photosensitizers may act as photocatalysts, not all photocatalysts may act as photosensitizers.
344:
Pictured from top to bottom, (A) benzophenone, (B) methylene blue, and (C) rose Bengal are all organic photosensitizers. All metals involved are purely
380:
from pi-electron accepting ligands. This interaction between the metal center and the ligand leads to a large continuum of orbitals within both the
113:
Basic schematic for all photosensitizers (PS) wherein the photosensitizer absorbs light (hν) and transfers energy to create a physicochemical change
109:
1545:
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964:
865:
1261:
Baptista, Mauricio S.; et al. (2017). "Type I and Type II Photosensitized
Oxidation Reactions: Guidelines and Mechanistic Pathways".
197:, where it then reacts with another chemical species. These photoinitiators are often completely chemically changed after their reaction.
1394:
Jiang Y, Weiss EA (September 2020). "Colloidal
Quantum Dots as Photocatalysts for Triplet Excited State Reactions of Organic Molecules".
1057:
Kavarnos GJ, Turro NJ (1986-04-01). "Photosensitization by reversible electron transfer: theories, experimental evidence, and examples".
45:, where it remains chemically intact, poised to absorb more light. One branch of chemistry which frequently utilizes photosensitizers is
2009:
Vignoni, Mariana; Rasse-Suriani, Federico A. O.; Butzbach, Kathrin; Erra-Balsells, Rosa; Epe, Bernd; Cabrerizo, Franco M. (2013-07-24).
890:
1033:
1000:
1676:"Tolyporphin: a natural product from cyanobacteria with potent photosensitizing activity against tumor cells in vitro and in vivo"
1172:
Julliard M, Chanon M (1983-08-01). "Photoelectron-transfer catalysis: its connections with thermal and electrochemical analogs".
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organometallic photosensitizers as well. Some relevant naturally occurring examples of organometallic photosensitizers include
377:
85:
and transfer absorbed energy into neighboring molecules. This absorption of light is made possible by photosensitizers' large
2107:
1561:
Lorente, Carolina; et al. (2021). "A model to understand type I oxidations of biomolecules photosensitized by pterins".
1210:
O'Regan B, Grätzel M (October 1991). "A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO 2 films".
547:
Dye sensitized solar cells are photosensitizers which transfer energy to semiconductors to generate energy from solar light
429:
425:
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inflammatory skin conditions in animals and have been observed to slightly reduce the minimum tanning dose in humans.
285:
97:. While many photosensitizers are organic or organometallic compounds, there are also examples of using semiconductor
697:
392:
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While many organometallic photosensitizer compounds are made synthetically, there also exists naturally occurring,
57:. Photosensitizers are also used to generate prolonged excited electronic states in organic molecules with uses in
1995:
Brockmoller J, et al. Hypericin and pseudohypericin: Pharmacokinetics and effects on photosensitivity in humans.
687:
667:
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70:
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reactions result in the photosensitizer being quenched by a different chemical substrate than molecular oxygen.
2112:
640:
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368:. These metals, as well as others, are common metal centers for photosensitizers due to their highly filled
303:
233:
34:
236:. However, it was not until the 1960s that the electron donating mechanism was confirmed through various
158:
The photosensitizer must impart a physicochemical change upon a substrate after absorbing incident light.
1705:
504:
1477:"Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis"
1785:
Tributsch H (1972). "Reaction of
Excited Chlorophyll Molecules at Electrodes and in Photosynthesis".
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388:(LUMO) which allows for excited electrons to switch multiplicities via intersystem crossing.
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Karimi M, Sahandi
Zangabad P, Baghaee-Ravari S, Ghazadeh M, Mirshekari H, Hamblin MR (April 2017).
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Some examples of photosensitizing medications (both investigatory and approved for human use) are:
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Morlière P, Mazière JC, Santus R, Smith CD, Prinsep MR, Stobbe CC, et al. (August 1998).
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763:"Atmospheric photosensitized heterogeneous and multiphase reactions: from outdoors to indoors"
521:. The resulting excited oxygen species then selectively degrades the tumor or cancerous mass.
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Upon imparting a chemical change, the photosensitizer returns to its original chemical form.
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331:(A) and Tris(2-phenylpyridine)iridium (B), two examples of organometallic photosensitizers.
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into another nearby molecule either directly or by a chemical reaction. Upon absorbing
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Zhang P, Huang H, Banerjee S, Clarkson GJ, Ge C, Imberti C, Sadler PJ (February 2019).
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Organometallic photosensitizers contain a metal atom chelated to at least one organic
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Gómez
Alvarez E, Wortham H, Strekowski R, Zetzsch C, Gligorovski S (February 2012).
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123:
42:
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1738:"Nucleus-Targeted Organoiridium-Albumin Conjugate for Photodynamic Cancer Therapy"
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undergo an irreversible change to become an acidic species upon light absorption.
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98:
82:
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Liu Y, Ma Y, Zhao Y, Sun X, Gándara F, Furukawa H, et al. (January 2016).
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molecule. This excites the oxygen molecule into the singlet state, making it a
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of radiation from incident light, photosensitizers transform into an excited
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1344:"Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light"
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908:"Weaving of organic threads into a crystalline covalent organic framework"
1958:
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1524:
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or cancerous masses. This discovery was first observed back in 1907 by
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Gollnick K (1968). "Type II Photooxygenation Reactions in Solution".
1097:
Daniell MD, Hill JS (May 1991). "A history of photodynamic therapy".
575:
500:
353:
127:
1710:"Simply shining light on dinosaur metal compound kills cancer cells"
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Photosensitizers have existed within natural systems for as long as
122:
Photosensitizers absorb light (hν) and transfer the energy from the
227:
analyzing the results of chemical reactions where photosensitizers
1945:
Zhou Q, Shi G (March 2016). "Conducting Polymer-Based Catalysts".
615:
611:
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284:
259:
78:
18:
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1028:(3rd ed.). Upper Saddle River, N.J.: Pearson/Prentice Hall.
2011:"Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines"
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material to generate electric energy output. These dyes act as
457:
quantum dots as photosensitizers includes their small, tunable
499:
utilizes Type II photosensitizers to harvest light to degrade
194:
165:
It is important to differentiate photosensitizers from other
729:. International Union of Pure and Applied Chemistry. 2014.
273:
There are two main pathways for photosensitized reactions.
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utilize these photosensitizer dyes to absorb photons from
536:
and, after being irradiated with light (a process called
570:
and transfer energy rich electrons to the neighboring
189:
absorb light to become a reactive species, commonly a
532:, creating a photosensitized molecule, can penetrate
524:
In February 2019, medical scientists announced that
512:
the patient's affected area. This light (preferably
240:
methods including reaction-intermediate studies and
1830:"Putting Photosystem I to Work: Truly Green Energy"
1337:
1335:
154:For a molecule to be considered a photosensitizer:
348:to keep the material in the solid state as a salt.
1099:The Australian and New Zealand Journal of Surgery
995:. Menlo Park, Calif.: Benjamin/Cummings Pub. Co.
808:
806:
1475:Prier CK, Rankic DA, MacMillan DW (July 2013).
33:are light absorbers that alter the course of a
49:, using photosensitizers in reactions such as
289:Diagram of a Type II photosensitized reaction
257:in synthetic chemistry, and cancer treatment.
8:
957:Spin crossover in transition metal compounds
885:(2nd ed.). London: Chapman & Hall.
492:Photodynamic therapy § Photosensitizers
264:Diagram of a Type I photosensitized reaction
169:interactions including, but not limited to,
138:then flips in its intrinsic spin state via
1563:Journal of Photochemistry and Photobiology
424:and the continuum of orbitals in both the
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1947:Journal of the American Chemical Society
1442:Journal of the American Chemical Society
1396:Journal of the American Chemical Society
1348:Journal of the American Chemical Society
850:IUPAC Compendium of Chemical Terminology
815:Journal of the American Chemical Society
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2076:Wisconsin Department of Health Services
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1306:ACS Applied Materials & Interfaces
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1024:Allcock HR, Lampe FW, Mark JE (2003).
767:Environmental Science & Technology
623:Biological effects of photosensitizers
619:properties required for the reaction.
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2064:
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1991:
1989:
1828:Teodor AH, Bruce BD (December 2020).
1532:. John Wiley & Sons, Ltd: 23–42.
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1143:. John Wiley & Sons, Ltd: 1–122.
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269:Types of photosensitization processes
134:. The single electron in the excited
69:. Generally, photosensitizers absorb
7:
2015:Organic & Biomolecular Chemistry
606:for their roles in the catalysis of
386:lowest unoccupied molecular orbital
1799:10.1111/j.1751-1097.1972.tb06297.x
1111:10.1111/j.1445-2197.1991.tb00230.x
382:highest occupied molecular orbital
16:Type of molecule reacting to light
14:
23:A photosensitizer being used in
1787:Photochemistry and Photobiology
1263:Photochemistry and Photobiology
993:Modern molecular photochemistry
378:metal to ligand charge transfer
315:Composition of photosensitizers
1026:Contemporary polymer chemistry
955:Gütlich P, Goodwin HA (2004).
1:
1924:10.1021/acs.inorgchem.7b03273
1847:10.1016/j.tibtech.2020.04.004
583:Hydrogen generating catalysts
540:), destroy the cancer cells.
89:, which lowers the energy of
1615:10.1021/acs.chemrev.6b00057
253:such as energy harvesting,
2129:
1575:10.1016/j.jpap.2021.100045
1526:Advances in Photochemistry
1137:Advances in Photochemistry
883:Polymer science dictionary
698:Light harvesting materials
564:Dye Sensitized Solar cells
557:Dye sensitized solar cells
489:
118:Mechanistic considerations
1999:1997;30(Suppl 2): 94-101.
1538:10.1002/9780470133316.ch2
1149:10.1002/9780470133361.ch1
688:Dye-sensitized solar cell
668:Artificial photosynthesis
71:electromagnetic radiation
53:, photocrosslinking, and
1834:Trends in Biotechnology
933:10.1126/science.aad4011
858:10.1351/goldbook.P04652
736:10.1351/goldbook.P04652
418:electron delocalization
306:. Upon excitation, the
304:reactive oxygen species
234:reactive oxygen species
79:visible light radiation
1872:Chemistry of Materials
1754:10.1002/anie.201813002
848:"Photosensitization".
548:
416:systems which promote
349:
332:
290:
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114:
87:de-localized π-systems
35:photochemical reaction
27:
2108:Drug delivery devices
1706:University of Warwick
546:
505:Hermann von Tappeiner
343:
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288:
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142:to become an excited
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101:as photosensitizers.
83:ultraviolet radiation
22:
1959:10.1021/jacs.5b12474
1454:10.1021/jacs.8b00742
1408:10.1021/jacs.0c07421
1360:10.1021/jacs.6b08313
959:. Berlin: Springer.
827:10.1021/jacs.8b00742
723:"Photosensitization"
693:Photoredox catalysis
678:Photodynamic therapy
608:pericyclic reactions
604:photoredox catalysts
597:Photoredox chemistry
538:photodynamic therapy
497:Photodynamic therapy
486:Photodynamic therapy
255:photoredox catalysis
250:aromatic hydrocarbon
207:Photoacid generators
140:Intersystem crossing
93:orbitals to promote
67:photodynamic therapy
37:. They usually are
25:photodynamic therapy
1912:Inorganic Chemistry
1708:(3 February 2019).
1402:(36): 15219–15229.
1224:1991Natur.353..737O
1186:10.1021/cr00056a003
1071:10.1021/cr00072a005
924:2016Sci...351..365L
779:2012EnST...46.1955G
592:Synthetic chemistry
579:they are attached.
376:counts, to promote
211:Photopolymerization
183:photopolymerization
63:photon upconversion
51:photopolymerization
2027:10.1039/C3OB40344K
1997:Pharmacopsychiatry
549:
350:
333:
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75:infrared radiation
28:
2021:(32): 5300–5309.
1884:10.1021/cm9036988
1840:(12): 1329–1342.
1742:Angewandte Chemie
1653:10.1021/nn102722z
1609:(17): 10075–166.
1547:978-0-470-13331-6
1493:10.1021/cr300503r
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1354:(13): 4584–4610.
1318:10.1021/am501192f
1275:10.1111/php.12716
1218:(6346): 737–740.
1158:978-0-470-13336-1
991:Turro NJ (1978).
966:978-3-540-40394-4
867:978-0-9678550-9-7
821:(18): 5934–5947.
788:10.1021/es2019675
656:Ethinyl estradiol
507:when he utilized
47:polymer chemistry
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1983:1989;17:257-261.
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1981:Tierarztl Prax
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401:Chlorophyll B
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327:Pictured are
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136:singlet state
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132:singlet state
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91:HOMO and LUMO
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1979:Kumper H. .
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534:cancer cells
528:attached to
523:
495:
476:Applications
468:
450:quantum dots
447:
444:Quantum dots
430:valence band
410:
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351:
318:
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246:
242:luminescence
221:
164:
153:
121:
99:quantum dots
43:ground state
30:
29:
1715:EurekAlert!
1284:11336/64008
1269:: 912–919.
703:Photoswitch
568:solar light
346:counterions
224:chlorophyll
2102:Categories
2082:2022-11-01
2036:11336/2178
1721:3 February
1569:: 100045.
709:References
610:and other
448:Colloidal
414:conjugated
374:d-electron
372:, or high
370:d-orbitals
203:Photoacids
179:photoacids
150:Parameters
2045:1477-0539
1892:0897-4756
1807:1751-1097
1424:221179722
1240:1476-4687
1194:0009-2665
1079:0009-2665
651:Amoxapine
616:oxidation
612:reduction
362:Ruthenium
244:studies.
39:catalysts
2053:23842892
1967:26863332
1932:29446925
1856:32448469
1815:94054808
1772:30552796
1661:21244012
1641:ACS Nano
1623:27285582
1511:23509883
1462:29671586
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975:56798940
942:26798010
852:. 2009.
835:29671586
797:22148293
662:See also
470:Nanorods
465:Nanorods
459:band gap
428:and the
422:band gap
1763:6468315
1692:9721863
1502:4028850
1369:5475407
1248:4340159
1220:Bibcode
1119:2025186
1011:4417476
920:Bibcode
912:Science
775:Bibcode
646:Doxepin
641:9-me-bc
576:dopants
530:albumin
526:iridium
481:Medical
407:Organic
366:Rhodium
358:Iridium
294:Type II
218:History
191:radical
128:photons
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354:ligand
277:Type I
193:or an
105:Theory
81:, and
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1420:S2CID
1244:S2CID
509:eosin
2049:PMID
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1963:PMID
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1888:ISSN
1852:PMID
1803:ISSN
1768:PMID
1723:2019
1688:PMID
1657:PMID
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