121:
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157:. 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.
263:
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
258:
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,
237:
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
629:
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
522:
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
589:
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
292:
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
467:
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
224:
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.
638:
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
422:
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
483:, 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.
612:
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
572:
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.
527:
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
598:
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.
443:
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.
431:. 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
1314:
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".
321:
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.
1880:
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".
216:(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.
52:. 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
330:
Photosensitizers can be placed into 3 generalized domains based on their molecular structure. These three domains are organometallic photosensitizers, organic photosensitizers, and nanomaterial photosensitizers.
1916:
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
242:
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
196:. 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.
367:. 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
1650:
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".
1451:
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".
824:
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".
309:
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,
472:
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.
212:
accelerate chemical reactions which rely upon light. While some photosensitizers may act as photocatalysts, not all photocatalysts may act as photosensitizers.
355:
Pictured from top to bottom, (A) benzophenone, (B) methylene blue, and (C) rose Bengal are all organic photosensitizers. All metals involved are purely
391:
from pi-electron accepting ligands. This interaction between the metal center and the ligand leads to a large continuum of orbitals within both the
124:
Basic schematic for all photosensitizers (PS) wherein the photosensitizer absorbs light (hν) and transfers energy to create a physicochemical change
120:
1556:
1167:
975:
876:
1272:
Baptista, Mauricio S.; et al. (2017). "Type I and Type II Photosensitized
Oxidation Reactions: Guidelines and Mechanistic Pathways".
208:, where it then reacts with another chemical species. These photoinitiators are often completely chemically changed after their reaction.
1405:
Jiang Y, Weiss EA (September 2020). "Colloidal
Quantum Dots as Photocatalysts for Triplet Excited State Reactions of Organic Molecules".
1068:
Kavarnos GJ, Turro NJ (1986-04-01). "Photosensitization by reversible electron transfer: theories, experimental evidence, and examples".
56:, where it remains chemically intact, poised to absorb more light. One branch of chemistry which frequently utilizes photosensitizers is
2020:
Vignoni, Mariana; Rasse-Suriani, Federico A. O.; Butzbach, Kathrin; Erra-Balsells, Rosa; Epe, Bernd; Cabrerizo, Franco M. (2013-07-24).
901:
1044:
1011:
1687:"Tolyporphin: a natural product from cyanobacteria with potent photosensitizing activity against tumor cells in vitro and in vivo"
1183:
Julliard M, Chanon M (1983-08-01). "Photoelectron-transfer catalysis: its connections with thermal and electrochemical analogs".
406:
organometallic photosensitizers as well. Some relevant naturally occurring examples of organometallic photosensitizers include
388:
96:
and transfer absorbed energy into neighboring molecules. This absorption of light is made possible by photosensitizers' large
2118:
1572:
Lorente, Carolina; et al. (2021). "A model to understand type I oxidations of biomolecules photosensitized by pterins".
1221:
O'Regan B, Grätzel M (October 1991). "A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO 2 films".
558:
Dye sensitized solar cells are photosensitizers which transfer energy to semiconductors to generate energy from solar light
440:
436:
639:
inflammatory skin conditions in animals and have been observed to slightly reduce the minimum tanning dose in humans.
296:
108:. While many photosensitizers are organic or organometallic compounds, there are also examples of using semiconductor
708:
403:
402:
While many organometallic photosensitizer compounds are made synthetically, there also exists naturally occurring,
68:. Photosensitizers are also used to generate prolonged excited electronic states in organic molecules with uses in
2006:
Brockmoller J, et al. Hypericin and pseudohypericin: Pharmacokinetics and effects on photosensitivity in humans.
698:
678:
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81:
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reactions result in the photosensitizer being quenched by a different chemical substrate than molecular oxygen.
2123:
651:
529:
379:. These metals, as well as others, are common metal centers for photosensitizers due to their highly filled
314:
244:
45:
247:. However, it was not until the 1960s that the electron donating mechanism was confirmed through various
169:
The photosensitizer must impart a physicochemical change upon a substrate after absorbing incident light.
1716:
515:
1488:"Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis"
1796:
Tributsch H (1972). "Reaction of
Excited Chlorophyll Molecules at Electrodes and in Photosynthesis".
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399:(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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774:"Atmospheric photosensitized heterogeneous and multiphase reactions: from outdoors to indoors"
532:. 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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30:
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342:(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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134:
53:
1934:
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1749:"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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109:
93:
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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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1355:"Smart Nanostructures for Cargo Delivery: Uncaging and Activating by Light"
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1021:
952:
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807:
1702:
1129:
919:"Weaving of organic threads into a crystalline covalent organic framework"
1969:
1612:
Romero NA, Nicewicz DA (September 2016). "Organic Photoredox Catalysis".
1535:
Bowen EJ (1963). "The Photochemistry of Aromatic Hydrocarbon Solutions".
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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".
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Daniell MD, Hill JS (May 1991). "A history of photodynamic therapy".
586:
511:
364:
138:
1721:"Simply shining light on dinosaur metal compound kills cancer cells"
233:
Photosensitizers have existed within natural systems for as long as
133:
Photosensitizers absorb light (hν) and transfer the energy from the
238:
analyzing the results of chemical reactions where photosensitizers
1956:
Zhou Q, Shi G (March 2016). "Conducting Polymer-Based Catalysts".
626:
622:
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519:
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295:
270:
89:
29:
2083:"Medications and other Agents that Increase Sensitivity to Light"
1039:(3rd ed.). Upper Saddle River, N.J.: Pearson/Prentice Hall.
2022:"Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines"
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material to generate electric energy output. These dyes act as
468:
quantum dots as photosensitizers includes their small, tunable
510:
utilizes Type II photosensitizers to harvest light to degrade
205:
176:
It is important to differentiate photosensitizers from other
740:. International Union of Pure and Applied Chemistry. 2014.
284:
There are two main pathways for photosensitized reactions.
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utilize these photosensitizer dyes to absorb photons from
547:
and, after being irradiated with light (a process called
581:
and transfer energy rich electrons to the neighboring
200:
absorb light to become a reactive species, commonly a
543:, creating a photosensitized molecule, can penetrate
535:
In February 2019, medical scientists announced that
523:
the patient's affected area. This light (preferably
251:
methods including reaction-intermediate studies and
1841:"Putting Photosystem I to Work: Truly Green Energy"
1348:
1346:
165:For a molecule to be considered a photosensitizer:
359:to keep the material in the solid state as a salt.
1110:The Australian and New Zealand Journal of Surgery
1006:. Menlo Park, Calif.: Benjamin/Cummings Pub. Co.
819:
817:
1486:Prier CK, Rankic DA, MacMillan DW (July 2013).
44:are light absorbers that alter the course of a
60:, using photosensitizers in reactions such as
300:Diagram of a Type II photosensitized reaction
268:in synthetic chemistry, and cancer treatment.
8:
968:Spin crossover in transition metal compounds
896:(2nd ed.). London: Chapman & Hall.
503:Photodynamic therapy § Photosensitizers
275:Diagram of a Type I photosensitized reaction
180:interactions including, but not limited to,
149:then flips in its intrinsic spin state via
1574:Journal of Photochemistry and Photobiology
435:and the continuum of orbitals in both the
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1958:Journal of the American Chemical Society
1453:Journal of the American Chemical Society
1407:Journal of the American Chemical Society
1359:Journal of the American Chemical Society
861:IUPAC Compendium of Chemical Terminology
826:Journal of the American Chemical Society
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2087:Wisconsin Department of Health Services
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1317:ACS Applied Materials & Interfaces
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1035:Allcock HR, Lampe FW, Mark JE (2003).
778:Environmental Science & Technology
634:Biological effects of photosensitizers
630:properties required for the reaction.
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2002:
2000:
1839:Teodor AH, Bruce BD (December 2020).
1543:. John Wiley & Sons, Ltd: 23–42.
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1154:. John Wiley & Sons, Ltd: 1–122.
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280:Types of photosensitization processes
145:. The single electron in the excited
80:. Generally, photosensitizers absorb
7:
2026:Organic & Biomolecular Chemistry
617:for their roles in the catalysis of
397:lowest unoccupied molecular orbital
1810:10.1111/j.1751-1097.1972.tb06297.x
1122:10.1111/j.1445-2197.1991.tb00230.x
393:highest occupied molecular orbital
27:Type of molecule reacting to light
25:
34:A photosensitizer being used in
1798:Photochemistry and Photobiology
1274:Photochemistry and Photobiology
1004:Modern molecular photochemistry
389:metal to ligand charge transfer
326:Composition of photosensitizers
1037:Contemporary polymer chemistry
966:Gütlich P, Goodwin HA (2004).
1:
1935:10.1021/acs.inorgchem.7b03273
1858:10.1016/j.tibtech.2020.04.004
594:Hydrogen generating catalysts
551:), destroy the cancer cells.
100:, which lowers the energy of
1626:10.1021/acs.chemrev.6b00057
264:such as energy harvesting,
2140:
1586:10.1016/j.jpap.2021.100045
1537:Advances in Photochemistry
1148:Advances in Photochemistry
894:Polymer science dictionary
709:Light harvesting materials
575:Dye Sensitized Solar cells
568:Dye sensitized solar cells
500:
129:Mechanistic considerations
2010:1997;30(Suppl 2): 94-101.
1549:10.1002/9780470133316.ch2
1160:10.1002/9780470133361.ch1
699:Dye-sensitized solar cell
679:Artificial photosynthesis
82:electromagnetic radiation
64:, photocrosslinking, and
1845:Trends in Biotechnology
944:10.1126/science.aad4011
869:10.1351/goldbook.P04652
747:10.1351/goldbook.P04652
429:electron delocalization
317:. Upon excitation, the
315:reactive oxygen species
245:reactive oxygen species
90:visible light radiation
18:Photosensitizing agents
1883:Chemistry of Materials
1765:10.1002/anie.201813002
859:"Photosensitization".
559:
427:systems which promote
360:
343:
301:
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125:
98:de-localized π-systems
46:photochemical reaction
38:
2119:Drug delivery devices
1717:University of Warwick
557:
516:Hermann von Tappeiner
354:
337:
299:
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153:to become an excited
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112:as photosensitizers.
94:ultraviolet radiation
33:
1970:10.1021/jacs.5b12474
1465:10.1021/jacs.8b00742
1419:10.1021/jacs.0c07421
1371:10.1021/jacs.6b08313
970:. Berlin: Springer.
838:10.1021/jacs.8b00742
734:"Photosensitization"
704:Photoredox catalysis
689:Photodynamic therapy
619:pericyclic reactions
615:photoredox catalysts
608:Photoredox chemistry
549:photodynamic therapy
508:Photodynamic therapy
497:Photodynamic therapy
266:photoredox catalysis
261:aromatic hydrocarbon
218:Photoacid generators
151:Intersystem crossing
104:orbitals to promote
78:photodynamic therapy
48:. They usually are
36:photodynamic therapy
1923:Inorganic Chemistry
1719:(3 February 2019).
1413:(36): 15219–15229.
1235:1991Natur.353..737O
1197:10.1021/cr00056a003
1082:10.1021/cr00072a005
935:2016Sci...351..365L
790:2012EnST...46.1955G
603:Synthetic chemistry
590:they are attached.
387:counts, to promote
222:Photopolymerization
194:photopolymerization
74:photon upconversion
62:photopolymerization
2038:10.1039/C3OB40344K
2008:Pharmacopsychiatry
560:
361:
344:
302:
277:
126:
86:infrared radiation
39:
2032:(32): 5300–5309.
1895:10.1021/cm9036988
1851:(12): 1329–1342.
1753:Angewandte Chemie
1664:10.1021/nn102722z
1620:(17): 10075–166.
1558:978-0-470-13331-6
1504:10.1021/cr300503r
1459:(18): 5934–5947.
1365:(13): 4584–4610.
1329:10.1021/am501192f
1286:10.1111/php.12716
1229:(6346): 737–740.
1169:978-0-470-13336-1
1002:Turro NJ (1978).
977:978-3-540-40394-4
878:978-0-9678550-9-7
832:(18): 5934–5947.
799:10.1021/es2019675
667:Ethinyl estradiol
518:when he utilized
58:polymer chemistry
16:(Redirected from
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1994:1989;17:257-261.
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66:photodegradation
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1691:Cancer Research
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1323:(10): 7876–84.
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929:(6271): 365–9.
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891:
890:
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858:
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853:
823:
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771:
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738:IUPAC Gold Book
732:
731:
727:
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675:
647:St. John's Wort
636:
610:
605:
596:
570:
565:
505:
499:
494:
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452:
437:conduction band
420:
395:(HOMO) and the
349:
328:
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231:
198:Photoinitiators
182:photoinitiators
163:
131:
118:
106:photoexcitation
28:
23:
22:
15:
12:
11:
5:
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2105:External links
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1996:
1992:Tierarztl Prax
1983:
1964:(9): 2868–76.
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465:semiconductor
462:
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449:Nanomaterials
447:
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412:Chlorophyll B
409:
408:Chlorophyll A
405:
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366:
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341:
340:Chlorophyll A
338:Pictured are
336:
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178:photochemical
171:
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155:triplet state
152:
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147:singlet state
144:
143:singlet state
140:
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103:
102:HOMO and LUMO
99:
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545:cancer cells
539:attached to
534:
506:
487:Applications
479:
461:quantum dots
458:
455:Quantum dots
441:valence band
421:
401:
362:
329:
308:
291:
283:
257:
253:luminescence
232:
175:
164:
132:
110:quantum dots
54:ground state
41:
40:
1726:EurekAlert!
1295:11336/64008
1280:: 912–919.
714:Photoswitch
579:solar light
357:counterions
235:chlorophyll
2113:Categories
2093:2022-11-01
2047:11336/2178
1732:3 February
1580:: 100045.
720:References
621:and other
459:Colloidal
425:conjugated
385:d-electron
383:, or high
381:d-orbitals
214:Photoacids
190:photoacids
161:Parameters
2056:1477-0539
1903:0897-4756
1818:1751-1097
1435:221179722
1251:1476-4687
1205:0009-2665
1090:0009-2665
662:Amoxapine
627:oxidation
623:reduction
373:Ruthenium
255:studies.
50:catalysts
2064:23842892
1978:26863332
1943:29446925
1867:32448469
1826:94054808
1783:30552796
1672:21244012
1652:ACS Nano
1634:27285582
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1055:51096012
986:56798940
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863:. 2009.
846:29671586
808:22148293
673:See also
481:Nanorods
476:Nanorods
470:band gap
439:and the
433:band gap
1774:6468315
1703:9721863
1513:4028850
1380:5475407
1259:4340159
1231:Bibcode
1130:2025186
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931:Bibcode
923:Science
786:Bibcode
657:Doxepin
652:9-me-bc
587:dopants
541:albumin
537:iridium
492:Medical
418:Organic
377:Rhodium
369:Iridium
305:Type II
229:History
202:radical
139:photons
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288:Type I
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116:Theory
92:, and
1822:S2CID
1431:S2CID
1255:S2CID
520:eosin
2060:PMID
2052:ISSN
1974:PMID
1939:PMID
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1863:PMID
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1779:PMID
1734:2019
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