photoswitch

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A photochromic compound can change its configuration or structure upon irradiation with light. Several examples of photochromic compounds include: azobenzene,{{cite journal | vauthors = Bandara HM, Burdette SC | title = Photoisomerization in different classes of azobenzene | journal = Chemical Society Reviews | volume = 41 | issue = 5 | pages = 1809–25 | date = March 2012 | pmid = 22008710 | doi = 10.1039/C1CS15179G }} spiropyran,{{cite journal | vauthors = Kortekaas L, Browne WR | title = The evolution of spiropyran: fundamentals and progress of an extraordinarily versatile photochrome | journal = Chemical Society Reviews | volume = 48 | issue = 12 | pages = 3406–3424 | date = June 2019 | pmid = 31150035 | doi = 10.1039/C9CS00203K | doi-access = free }} merocyanine,{{cite journal | vauthors = Klajn R | title = Spiropyran-based dynamic materials | journal = Chemical Society Reviews | volume = 43 | issue = 1 | pages = 148–84 | date = January 2014 | pmid = 23979515 | doi = 10.1039/C3CS60181A | doi-access = free }} diarylethene,{{cite journal| vauthors = Pu SZ, Sun Q, Fan CB, Wang RJ, Liu G |date=2016-04-14|title=Recent advances in diarylethene-based multi-responsive molecular switches |journal=Journal of Materials Chemistry C | volume=4|issue=15|pages=3075–3093|doi=10.1039/C6TC00110F|issn=2050-7534}} spirooxazine,{{cite journal | vauthors = Berkovic G, Krongauz V, Weiss V | title = Spiropyrans and Spirooxazines for Memories and Switches | journal = Chemical Reviews | volume = 100 | issue = 5 | pages = 1741–1754 | date = May 2000 | pmid = 11777418 | doi = 10.1021/cr9800715 }} fulgide,{{cite journal | vauthors = Yokoyama Y | title = Fulgides for Memories and Switches | journal = Chemical Reviews | volume = 100 | issue = 5 | pages = 1717–1740 | date = May 2000 | pmid = 11777417 | doi = 10.1021/cr980070c }} hydrazone,{{cite journal | vauthors = Su X, Aprahamian I | title = Hydrazone-based switches, metallo-assemblies and sensors | journal = Chemical Society Reviews | volume = 43 | issue = 6 | pages = 1963–81 | date = March 2014 | pmid = 24429467 | doi = 10.1039/C3CS60385G | doi-access = free }} nobormadiene,{{cite journal | vauthors = Orrego-Hernández J, Dreos A, Moth-Poulsen K | title = Engineering of Norbornadiene/Quadricyclane Photoswitches for Molecular Solar Thermal Energy Storage Applications | journal = Accounts of Chemical Research | volume = 53 | issue = 8 | pages = 1478–1487 | date = August 2020 | pmid = 32662627 | pmc = 7467572 | doi = 10.1021/acs.accounts.0c00235 }} thioindigo,{{cite journal | vauthors = Navrátil R, Wiedbrauk S, Jašík J, Dube H, Roithová J | title = Transforming hemithioindigo from a two-way to a one-way molecular photoswitch by isolation in the gas phase | journal = Physical Chemistry Chemical Physics | volume = 20 | issue = 10 | pages = 6868–6876 | date = March 2018 | pmid = 29485646 | doi = 10.1039/C8CP00096D | bibcode = 2018PCCP...20.6868N }} acrylamide-azobenzene-quaternary ammonia,{{cite journal | vauthors = Polosukhina A, Litt J, Tochitsky I, Nemargut J, Sychev Y, De Kouchkovsky I, Huang T, Borges K, Trauner D, Van Gelder RN, Kramer RH | display-authors = 6 | title = Photochemical restoration of visual responses in blind mice | language = English | journal = Neuron | volume = 75 | issue = 2 | pages = 271–82 | date = July 2012 | pmid = 22841312 | doi = 10.1016/j.neuron.2012.05.022 | pmc = 3408583 }} donor-acceptor Stenhouse adducts,{{cite journal | vauthors = Lerch MM, Szymański W, Feringa BL | title = The (photo)chemistry of Stenhouse photoswitches: guiding principles and system design | journal = Chemical Society Reviews | volume = 47 | issue = 6 | pages = 1910–1937 | date = March 2018 | pmid = 29468232 | doi = 10.1039/C7CS00772H | url = https://research.rug.nl/en/publications/b797d4e1-076e-4258-b853-e45a6faa5a42 }}{{Cite journal |last1=Helmy |first1=Sameh |last2=Oh |first2=Saemi |last3=Leibfarth |first3=Frank A. |last4=Hawker |first4=Craig J. |last5=Read de Alaniz |first5=Javier |date=2014-12-05 |title=Design and Synthesis of Donor–Acceptor Stenhouse Adducts: A Visible Light Photoswitch Derived from Furfural |url=https://pubs.acs.org/doi/10.1021/jo502206g |journal=The Journal of Organic Chemistry |language=en |volume=79 |issue=23 |pages=11316–11329 |doi=10.1021/jo502206g |pmid=25390619 |issn=0022-3263}} stilbene,{{cite journal| vauthors = Abourashed EA |date=2017-02-24|title=Review of Stilbenes: Applications in Chemistry, Life Sciences and Materials Science |journal=Journal of Natural Products|volume=80|issue=2|pages=577|doi=10.1021/acs.jnatprod.7b00089|issn=0163-3864}} etc.

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 transit 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.{{cite book| vauthors = Roberts JD, Caserio MC |url=https://resolver.caltech.edu/CaltechBOOK:1977.001|title=Basic Principles of Organic Chemistry, second edition|date=1977-05-15|publisher=W. A. Benjamin, Inc.|isbn=978-0-8053-8329-4|location=Menlo Park, CA}}

Although the mechanism for photoisomerization is still debated amongst most scientists, increasing evidence supports cis-/trans- isomerization of polyenes favoring the hula twist rather than the one-bond-flip.{{cite journal | vauthors = Liu RS | title = Photoisomerization by hula-twist: a fundamental supramolecular photochemical reaction | journal = Accounts of Chemical Research | volume = 34 | issue = 7 | pages = 555–62 | date = July 2001 | pmid = 11456473 | doi = 10.1021/ar000165c }} The one-bond-flip isomerizes at the reactive double bond while the hula twist undergoes a conformational isomerization at the adjacent single bond. However, the interconversion of stereoisomers of stilbene proceeds via one-bond-flip.{{cite journal | vauthors = Liu RS, Hammond GS | title = The case of medium-dependent dual mechanisms for photoisomerization: one-bond-flip and hula-twist | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 97 | issue = 21 | pages = 11153–8 | date = October 2000 | pmid = 11016972 | doi = 10.1073/pnas.210323197 | pmc = 17169 | bibcode = 2000PNAS...9711153L | doi-access = free }}

File:Understanding_Photoisomerization_from_the_Photoisomerization_from_A_to_B.png

One of the most important properties of a photoswitch is its quantum yield which measures the effectiveness of absorbed light to induce photoisomerization. Quantum yield is modeled and calculated using Arrhenius kinetics.{{cite journal | vauthors = Stranius K, Börjesson K | title = Determining the Photoisomerization Quantum Yield of Photoswitchable Molecules in Solution and in the Solid State | journal = Scientific Reports | volume = 7 | issue = 1 | pages = 41145 | date = January 2017 | pmid = 28117426 | doi = 10.1038/srep41145 | pmc = 5259717 | bibcode = 2017NatSR...741145S }} 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.{{cite journal| vauthors = Gonzalez A, Kengmana ES, Fonseca MV, Han GG | date = June 2020 |title=Solid-state photoswitching molecules: structural design for isomerization in condensed phase |journal=Materials Today Advances | volume=6 |pages=100058 |doi=10.1016/j.mtadv.2020.100058 |doi-access=free }} Through chemical modification, red shifting the wavelengths of absorption needed to cause isomerization leads to low light induced switching which has applications in photopharmacology.{{cite journal | vauthors = Wegner HA | title = Azobenzenes in a new light-switching in vivo | journal = Angewandte Chemie | volume = 51 | issue = 20 | pages = 4787–8 | date = May 2012 | pmid = 22461191 | doi = 10.1002/anie.201201336 }}

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.{{cite journal | vauthors = Dorel R, Feringa BL | title = Photoswitchable catalysis based on the isomerisation of double bonds | journal = Chemical Communications | volume = 55 | issue = 46 | pages = 6477–6486 | date = June 2019 | pmid = 31099809 | doi = 10.1039/C9CC01891C | doi-access = free }} As one of the most widely studied photoswitches, azobenzene has been shown to be 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.{{cite journal | vauthors = Roelz M, Butschke B, Breit B | title = Azobenzene-Integrated NHC Ligands: A Versatile Platform for Visible-Light-Switchable Metal Catalysis | journal = Journal of the American Chemical Society | volume = 146 | issue = 19 | pages = 13210–13225 | date = May 2024 | pmid = 38709955 | doi = 10.1021/jacs.4c01138 | doi-access = free }}

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One of the more prevalent biological examples in the human body that undergoes structural changes upon light irradiation includes the class of membrane-bound photoreceptors, Rhodopsins.{{cite journal | vauthors = Ernst OP, Lodowski DT, Elstner M, Hegemann P, Brown LS, Kandori H | title = Microbial and animal rhodopsins: structures, functions, and molecular mechanisms | journal = Chemical Reviews | volume = 114 | issue = 1 | pages = 126–63 | date = January 2014 | pmid = 24364740 | pmc = 3979449 | doi = 10.1021/cr4003769 }} These include the regulation of melanocytes, vision, the release of melatonin and the control of the circadian rhythm, etc.{{cite web|title=Photochemical reaction {{!}} chemical reaction|url=https://www.britannica.com/science/photochemical-reaction|access-date=|website=Encyclopedia Britannica|language=en}} Rhodopsins are highly efficient photochromic compounds that can undergo fast photoisomerization and are associated with various retinal proteins{{cite journal | vauthors = Inuzuka K, Becker RS | title = Mechanism of photoisomerization in the retinals and implications in rhodopsin | journal = Nature | volume = 219 | issue = 5152 | pages = 383–5 | date = July 1968 | pmid = 5667083 | doi = 10.1038/219383a0 | bibcode = 1968Natur.219..383I | s2cid = 4160990 }} along with light-gated channels and pumps in microbes.{{cite journal | vauthors = Kandori H | title = Biophysics of rhodopsins and optogenetics | journal = Biophysical Reviews | volume = 12 | issue = 2 | pages = 355–361 | date = April 2020 | pmid = 32065378 | pmc = 7242518 | doi = 10.1007/s12551-020-00645-0 }}

Advances in vision restoration with photochromic compounds has been investigated. Fast isomerization allows retinal cells to turn on when activated by light and advances in acrylamide-azobenzene-quaternary ammonia'' have shown restoration of visual responses in blind mice.{{cite journal | vauthors = Polosukhina A, Litt J, Tochitsky I, Nemargut J, Sychev Y, De Kouchkovsky I, Huang T, Borges K, Trauner D, Van Gelder RN, Kramer RH | display-authors = 6 | title = Photochemical restoration of visual responses in blind mice | journal = Neuron | volume = 75 | issue = 2 | pages = 271–82 | date = July 2012 | pmid = 22841312 | doi = 10.1016/j.neuron.2012.05.022 | pmc = 3408583 }} Companies involved in this area include Novartis, Vedere, Allergan, and Nanoscope Therapeutics.{{cite journal | vauthors = Ratner M | title = Light-activated genetic therapy to treat blindness enters clinic | journal = Nature Biotechnology | volume = 39 | issue = 2 | pages = 126–127 | date = February 2021 | pmid = 33564161 | doi = 10.1038/s41587-021-00823-9 | doi-access = }}

Through the incorporation of photoswitches into biological molecules, biological processes can be regulated through controlled 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.{{cite journal | vauthors = Szymański W, Beierle JM, Kistemaker HA, Velema WA, Feringa BL | title = Reversible photocontrol of biological systems by the incorporation of molecular photoswitches | journal = Chemical Reviews | volume = 113 | issue = 8 | pages = 6114–78 | date = August 2013 | pmid = 23614556 | doi = 10.1021/cr300179f | doi-access = free }} For example, optical control of ligand binding in human serum albumin has been demonstrated to influence its allosteric binding properties.{{cite journal | vauthors = Putri RM, Zulfikri H, Fredy JW, Juan A, Tananchayakul P, Cornelissen JJ, Koay MS, Filippi C, Katsonis N | display-authors = 6 | title = Photoprogramming Allostery in Human Serum Albumin | journal = Bioconjugate Chemistry | volume = 29 | issue = 7 | pages = 2215–2224 | date = July 2018 | pmid = 29975051 | pmc = 6053643 | doi = 10.1021/acs.bioconjchem.8b00184 }} Also, red-shifted azobenzenes have been used to control ionotropic glutamate receptors.{{cite journal | vauthors = Kienzler MA, Reiner A, Trautman E, Yoo S, Trauner D, Isacoff EY | title = A red-shifted, fast-relaxing azobenzene photoswitch for visible light control of an ionotropic glutamate receptor | journal = Journal of the American Chemical Society | volume = 135 | issue = 47 | pages = 17683–6 | date = November 2013 | pmid = 24171511 | pmc = 3990231 | doi = 10.1021/ja408104w }}

Photoswitches are studied in biology, materials chemistry, and physics and have a wide variety of potential applications, especially in the framework of nanotechnology.{{cite journal| vauthors = Sinicropi A |date=|title=Biomimetic Photoswitches |journal=Inorganica Chimica Acta|volume=470|pages=360–364|doi=10.1016/j.ica.2017.08.041|issn=0020-1693}}

Depending on the isomeric state, photoswitches have the potential to replace transistors used in electronics.{{cite web|title=The future of electronics is photoswitches|url=https://www.brandeis.edu/now/2019/february/photoswitch-electronic-han.html|access-date=|website=BrandeisNOW|language=en}} Through the attachment of photoswitches onto the surfaces of various 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.{{cite journal | vauthors = Goulet-Hanssens A, Eisenreich F, Hecht S | title = Enlightening Materials with Photoswitches | journal = Advanced Materials | volume = 32 | issue = 20 | pages = e1905966 | date = May 2020 | pmid = 31975456 | doi = 10.1002/adma.201905966 | bibcode = 2020AdM....3205966G | doi-access = free }}

Diarylethenes form stable molecular conduction junctions when placed between graphene electrodes at low and room temperature and act as a photo-electrical switch.{{cite journal | vauthors = Jia C, Migliore A, Xin N, Huang S, Wang J, Yang Q, Wang S, Chen H, Wang D, Feng B, Liu Z, Zhang G, Qu DH, Tian H, Ratner MA, Xu HQ, Nitzan A, Guo X | display-authors = 6 | title = Covalently bonded single-molecule junctions with stable and reversible photoswitched conductivity | journal = Science | volume = 352 | issue = 6292 | pages = 1443–5 | date = June 2016 | pmid = 27313042 | doi = 10.1126/science.aaf6298 | bibcode = 2016Sci...352.1443J | s2cid = 206649097 }} By combining a photoswitch, containing various highest and lowest unoccupied molecular orbital 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. A photo-electric cell is connected to a circuit that measures how much electricity the cell generates. The circuit decides and gives the output, according to the setting of minimum and maximum lux level.{{cite web|author-first=Chris|author-last=Woodford|author-link=Chris Woodford (author)|title=How do photoelectric cells work?|url=http://www.explainthatstuff.com/how-photoelectric-cells-work.html|access-date=|website=Explain that Stuff|date=4 December 2009 }}

Photoswitches have been used in the generation of three-dimensional animations and images.{{cite journal | vauthors = Patel SK, Cao J, Lippert AR | title = A volumetric three-dimensional digital light photoactivatable dye display | journal = Nature Communications | volume = 8 | pages = 15239 | date = July 2017 | pmid = 28695887 | pmc = 5508202 | doi = 10.1038/ncomms15239 | bibcode = 2017NatCo...815239P }} The display utilizes a medium composed of a class of photoswitches (known as spirhodamines) and digital light processing 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.

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.{{cite journal| vauthors = Sun CL, Wang C, Boulatov R |date=2019|title=Applications of Photoswitches in the Storage of Solar Energy |journal=ChemPhotoChem | volume=3|issue=6|pages=268–283|doi=10.1002/cptc.201900030|s2cid=155439646 |issn=2367-0932}}

Merocyanine 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, a storage potential and pH gradient were generated.{{cite journal | vauthors = Goulet-Hanssens A, Eisenreich F, Hecht S | title = Enlightening Materials with Photoswitches | journal = Advanced Materials | volume = 32 | issue = 20 | pages = e1905966 | date = May 2020 | pmid = 31975456 | doi = 10.1002/adma.201905966 | bibcode = 2020AdM....3205966G | doi-access = free }}

Incorporation of photoswitchable molecules into porous metal organic frameworks that can 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.

Incorporation of photoswitching molecules such as donor-acceptor Stenhouse adducts into polymersomes has been used to form nanoparticles which can selectively expose enzymes in response to light, allowing them to mimic some functions of cells.{{Cite journal |last1=Rifaie-Graham |first1=Omar |last2=Yeow |first2=Jonathan |last3=Najer |first3=Adrian |last4=Wang |first4=Richard |last5=Sun |first5=Rujie |last6=Zhou |first6=Kun |last7=Dell |first7=Tristan N. |last8=Adrianus |first8=Christopher |last9=Thanapongpibul |first9=Chalaisorn |last10=Chami |first10=Mohamed |last11=Mann |first11=Stephen |last12=de Alaniz |first12=Javier Read |last13=Stevens |first13=Molly M. |date=2022-11-07 |title=Photoswitchable gating of non-equilibrium enzymatic feedback in chemically communicating polymersome nanoreactors |journal=Nature Chemistry |volume=15 |issue=1 |language=en |pages=110–118 |doi=10.1038/s41557-022-01062-4 |pmid=36344820 |pmc=9836937 |issn=1755-4349|doi-access=free }}

Chiral shape driven transformations in liquid crystal structures can be achieved through photoisomerization of bistable hydrazones to generate long term stable polymer shapes.{{cite journal | vauthors = Ryabchun A, Li Q, Lancia F, Aprahamian I, Katsonis N | title = Shape-Persistent Actuators from Hydrazone Photoswitches | journal = Journal of the American Chemical Society | volume = 141 | issue = 3 | pages = 1196–1200 | date = January 2019 | pmid = 30624915 | pmc = 6346373 | doi = 10.1021/jacs.8b11558 }} Light-gated optical windows that can change the absorbance properties can be made by chirally doping liquid crystals with hydrazone photoswitches or by kinetically trapping various cholesteric states as a function of the photostationary state.{{cite journal | vauthors = Moran MJ, Magrini M, Walba DM, Aprahamian I | title = Driving a Liquid Crystal Phase Transition Using a Photochromic Hydrazone | journal = Journal of the American Chemical Society | volume = 140 | issue = 42 | pages = 13623–13627 | date = October 2018 | pmid = 30293432 | doi = 10.1021/jacs.8b09622 | s2cid = 207195468 }} Incorporation of photoswitches into nematic liquid crystals can change self-assembly, crystal packing, and the light reflecting properties of the supramolecular interactions.{{cite journal | vauthors = Zhang X, Koz B, Bisoyi HK, Wang H, Gutierrez-Cuevas KG, McConney ME, Bunning TJ, Li Q | display-authors = 6 | title = Electro- and Photo-Driven Orthogonal Switching of a Helical Superstructure Enabled by an Axially Chiral Molecular Switch | journal = ACS Applied Materials & Interfaces | volume = 12 | issue = 49 | pages = 55215–55222 | date = December 2020 | pmid = 33237715 | doi = 10.1021/acsami.0c19527 | s2cid = 227174963 | hdl = 11492/3985 | hdl-access = free }}

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.{{cite web| vauthors = Rosenbaum LC |date=November 7, 2018|title=Organic Photochromic Compounds|url=https://www.chemie.uni-konstanz.de/typo3temp/secure_downloads/82022/0/722a107bc9cf8d10f0c3c5388b2f8d886578e2a4/Rosenbaum_Organic-Photochromic-Compounds.pdf|website=Universitat Konstanz}} Novel azo-carrying photoswitches are introduced as molecular hinges,{{cite journal| vauthors = Kazem-Rostami M, Moghanian A |date=2017|title=Hünlich base derivatives as photo-responsive Λ-shaped hinges|journal=Organic Chemistry Frontiers|volume=4|issue=2|pages=224–228|doi=10.1039/C6QO00653A}}{{cite journal | vauthors = Norikane Y, Tamaoki N | title = Light-driven molecular hinge: a new molecular machine showing a light-intensity-dependent photoresponse that utilizes the trans-cis isomerization of azobenzene | journal = Organic Letters | volume = 6 | issue = 15 | pages = 2595–8 | date = July 2004 | pmid = 15255699 | doi = 10.1021/ol049082c }} which can be used in the design of molecular machines and optical devices.{{cite journal| vauthors = Kazem-Rostami M |date=5 December 2016|title=Design and Synthesis of Ʌ-Shaped Photoswitchable Compounds Employing Tröger's Base Scaffold|journal=Synthesis|volume=49|issue=6|pages=1214–1222|doi=10.1055/s-0036-1588913|s2cid=99913657 }}

In the field of photopharmacology, photoswitches are being investigated as a means to control activity. By including a photoswitch in a drug, the drug assumes several biological active states. Light can be used to switch between these states, resulting in remote control of a drug's activity. Photoswitches have also been shown modulate surface energy properties which can control how the photoswitchable shell interacts with nanoparticles.{{cite journal|vauthors=Velema WA, Szymanski W, Feringa BL|date=February 2014|title=Photopharmacology: beyond proof of principle|url=https://pure.rug.nl/ws/files/13153399/ja_2013_13063e_photopharma_revised.pdf|journal=Journal of the American Chemical Society|volume=136|issue=6|pages=2178–91|doi=10.1021/ja413063e|pmid=24456115|hdl=11370/d6714f52-c2c8-4e48-b345-238e98bcc776|s2cid=197196311 |hdl-access=free}} 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.{{cite journal| vauthors = Guo X, Shao B, Zhou S, Aprahamian I, Chen Z |date=2020-03-18|title=Visualizing intracellular particles and precise control of drug release using an emissive hydrazone photochrome |journal=Chemical Science | volume=11|issue=11|pages=3016–3021|doi=10.1039/C9SC05321B|pmid=34122804|pmc=8157519|issn=2041-6539|doi-access=free}}

Photoswitches have been investigated 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.

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Category:Switches