Wavelength-selective light-matter interactions in polymer science
نویسندگان
چکیده
Light has provided unparalleled control over when and where chemical transformations take place (spatiotemporal control), yet a third dimension emerged the incident color of light can tailor reactivity, termed here spectral control. Wavelength-selectivity in polymer science been influenced by pioneering reports light-driven isomerization (photoswitches), deprotection (photocages), coupling (cycloaddition/-reversion), electron/energy transfer (photoredox/-sensitization), which enabled both soft matter fabrication property manipulation (e.g., mechanical, optical, electrical). Advancing utilizing wavelength-selective will rely on (1) characterizing photochemical reactions quantitatively as function wavelength, (2) introducing new reactive chromophores, (3) expanding mechanistic scope manufacturing beyond light-induced radical reactions, (4) manipulating material properties outside mechanical. Going forward, these facilitate design next-generation “smart” materials, have advanced tailored for applications that range from tissue engineering robotics to electronics. prominent stimulus generate manipulate polymeric materials across multiple length scales. Compared with other external stimuli, light-mediated approaches enable unprecedented occur (i.e., spatiotemporal control). To date, majority established protocols individual wavelengths (?monochromatic), does not harness full potential light-matter interactions. This review summarizes nascent progress discrete tool create alter matter. The concepts are structured an effort provide roadmap foster directions light-based chemistry. physical organic nature wavelength selectivity is first detailed introduction key insight lay foundation further developments. Next, overview chromophores undergo various presented, followed their utility platforms controlled synthesis, manipulation, manufacturing. concludes summary outlook exciting future interactions science. Throughout history, there several dramatic paradigm shifts understanding (Figure 1).1Feynman R.P. Leighton R.B. Sands M.L. Feynman Lectures Physics New Millennium. Basic Books, 2011Google Scholar In 1700s, Newton passed sunlight through prism this experiment deduced was stream particles. second half 19th century, Maxwell described electromagnetic waves using set elegant equations (Maxwell's equations). 1905, Einstein built Planck's theory energy quanta categorizing quantized (photons) explain “photoelectric effect,” phenomenon describing emission electrons upon interaction radiation, such light.2Einstein A. Über einen die Erzeugung und Verwandlung des Lichtes betreffenden heuristischen Gesichtspunkt.Ann. Phys. 1905; 322: 132-148Crossref Scopus (851) Google ultimately led recognition wave-particle duality de Broglie 1924.3Broglie L.de XXXV. A tentative quanta.Lond. Edinb. Dublin Philos. Mag. J. Sci. 1924; 47: 446-458Crossref Together, transformative discoveries connected photon (E) (?) corresponding wave (Equation 1).E=hv? h: constant; v: speed vacuum(Equation 1) practical date back 1826, discovery Joseph Nicéphore Niépce resulted permanent image nature.4Willson C.G. Dammel R.R. Reiser Photoresist materials: historical perspective.in: Fuller G.E. Proc. SPIE 3051, Optical Microlithography X. SPIE, 1997https://doi.org/10.1117/12.275984Google It also time demonstrated give reaction occurs Today, plays central role myriad commercialized emergent technologies, photography, coatings, adhesives microelectronics three-dimensional (3D) printing. Since inception everlasting discoveries, chemistry, or molecular photochemistry, subject immense research efforts, especially development compounds demonstrate distinct absorption and/or scattering) light.5Turro N.J. Ramamurthy V. Scaiano J.C. Modern Molecular Photochemistry Organic Molecules. University Science 2010Google Mechanistically, photons raises higher excited state capable undergoing (Scheme 1). stimuli (redox, heat, pH, electricity), photoexcitation affords 1), while additionally offering avenue toward control.6Aubert S. Bezagu M. Spivey A.C. Arseniyadis Spatial temporal processes.Nat. Rev. Chem. 2019; 3: 706-722Crossref (14) last few decades, substantial advances synthesis characterization chromophores. However, utilize single non-discrete broadband UV visible spectra) near monochromatic narrow distribution, light-emitting diode [LED]).7Corrigan N. Shanmugam Xu Boyer C. Photocatalysis synthesis.Chem. Soc. 2016; 45: 6165-6212Crossref PubMed Scholar, 8Xiao P. Zhang Dumur F. Tehfe M.A. Morlet-Savary Graff B. Gigmes D. Fouassier J.P. Lalevée Visible sensitive photoinitiating systems: recent cationic photopolymerization under conditions.Prog. Polym. 2015; 41: 32-66Crossref (294) 9Zivic Kuroishi P.K. Dove A.P. Sardon H. Recent challenges photoacid photobase generators polymerizations.Angew. Int. Ed. 58: 10410-10422Crossref (40) 10Dadashi-Silab Doran Yagci Y. Photoinduced electron macromolecular syntheses.Chem. 116: 10212-10275Crossref (434) 11Tuten B.T. Wiedbrauk Barner-Kowollik Contemporary catalyst-free photochemistry synthetic science.Prog. 2020; 100: 101183Crossref (13) fully exploit within materials/polymers, it necessary establish multi-chromatic processes mediated different (or colors) light. may be accomplished bidirectional pathways switch between two states chromophore disparate selectively activated Upon exposure (?1 ?2), fall into one three general categories: E/Z 2A),12Hartley G.S. cis-form azobenzene.Nature. 1937; 140: 281Crossref Scholar,13Bandara H.M.D. Burdette S.C. Photoisomerization classes azobenzene.Chem. 2012; 1809-1825Crossref (1457) ring opening 2B),14Hirshberg Fischer E. Photochromism reversible internal transitions some spiropyrans at low temperatures. Part I.J. (Resumed). 1954; 297: 3129-3137Crossref Scholar,15Kortekaas L. Browne W.R. evolution spiropyran: fundamentals extraordinarily versatile photochrome.Chem. 48: 3406-3424Crossref dimerization 2C).16Ström K.T. Polymere cumarsäuren.Berichte Dtsch. Ges. 1904; 37: 1383-1386Crossref (7) Scholar,17Kaur G. Johnston Saito K. Photo-reversible dimerisation systems.Polym. 2014; 5: 2171-2186Crossref Wavelength-orthogonal (no cross-reactivity) activation induce/control reactant product versus B B) attractive mode expand accessible materials.5Turro orthogonality each remains formidable challenge 2A ).18Corrigan Yeow Judzewitsch Seeing light: advancing chemistry photopolymerization.Angew. 5170-5189Crossref (180) 19Frisch Marschner D.E. Goldmann A.S. Wavelength-Gated dynamic covalent chemistry.Angew. 2018; 57: 2036-2045Crossref (56) 20Corrigan Ciftci Jung Mediating science.Angew. 2021; 60: 1748-1781Crossref (15) 21Corrigan 100th anniversary viewpoint: modern science.ACS Macro Lett. 8: 812-818Crossref (35) general, rules guide orthogonal system comprising (Ca Cb): selective electronic mismatch preclude reactants present photosystem co-initiator(s)).19Frisch Scholar,22Hansen M.J. Velema W.A. Lerch M.M. Szymanski W. Feringa B.L. Wavelength-selective cleavage photoprotecting groups: strategies systems.Chem. 44: 3358-3377Crossref By avoiding source, rule #1 guarantees Cb) simultaneously 2B). critical consider strength absorption, molar absorptivity ? 2, Beer's law), well quantum yield ? 3), process.23San Miguel Bochet del Campo caged surfaces: how many functional levels possible?.J. Am. 2011; 133: 5380-5388Crossref (0) Scholar?=Al×cA: absorbance; l: optical path length; c: concentration chromophore(Equation 2) ?=Number molecules reactedNumber absorbed(Equation 3) Notably, necessarily predict reactivity specific yield), selecting based solely spectrum provides only limited guidance. Instead, optimal excitation identified employing tunable sources screen reaction's conversion constant flux wavelength-dependent photoreactivity spectra, so-called action plots photoreactivity.19Frisch Scholar,24Menzel Noble B.B. Lauer Coote Blinco Wavelength dependence cycloadditions.J. 2017; 139: 15812-15820Crossref (50) Scholar25Menzel Predicting selectivity.Nat Commun. 12: 1691Crossref mitigating crossover (electron/energy transfer) ground (Ca? Cb, Ca Cb?, Ca? Cb?) careful design, #2 fulfilled 2C). An additional consideration include either singlet triplet levels, modes cross-communication possible. Furthermore, photosystems operating visible-to-near-infrared (NIR) region separate molecule co-initiator), oxidized reduced species all components involved need considered designing wavelength-orthogonal reactions. Although excluded thermodynamically, conform anything but trivial.26Lerch Hansen Orthogonal photoswitching multifunctional system.Nat. 7: 12054Crossref (101) Therefore, kinetic driving discussed, meaning those do abide inducing/controlling desired frame, wavelength-selective. includes stepwise photomediated vessel toggling source wavelengths, usually long (lower energy) short (higher 3). wavelength-orthogonal/selective undoubtedly augment toolbox more sophisticated structures, inspired nature, including hierarchical architectures fine-tuned multi-functionality. highlights literature demonstrates science, capabilities challenges, inform invigorate innovation. next section readers build-upon research, focuses developed photocontrolled polymerization, permit well-defined polymers mechanisms. fourth turns optoelectronic, ion-transport, mechanical), biomaterials. penultimate emphasizes photolithography 3D printing, we conclude perspective opportunities area. irradiation parameter used transformations. Through selection triggered, containing states/isomers than access redox states. profile thought unique blueprint intrinsic particular conditions matrix polarity temperature), magnitude (molar absorptivity) given correlates likelihood result event. increased correlate any wavelength.19Frisch section, snapshot spanning (100–400 nm) (400–780 discussed overarching classes: photoswitches, photoremovable protecting groups, (ir)reversible coupling. photoswitches small reversibly isomerize irradiation. photoswitch alters its geometry ?-conjugation formation dissociation bonds. Accordingly, physicochemical change “ON” “OFF”. Parameters interest mentioned rate reversibility, photochromism (color change), change, fatigue resistance, operational range, emphasis latter connection selectivity. main photoisomerization fascinating effects cis/trans Z/E) electrocyclization/ring opening. For comprehensive discussion refer following published reviews.13Bandara Scholar,27Irie Fukaminato T. Matsuda Kobatake diarylethene crystals: memories, switches, actuators.Chem. 114: 12174-12277Crossref (1345) 28Lerch Szyma?ski (photo)chemistry Stenhouse photoswitches: guiding principles design.Chem. 1910-1937Crossref 29Crespi Simeth N.A. König Heteroaryl azo dyes photoswitches.Nat. 133-146Crossref (90) 30Fihey Perrier Jacquemin Multiphotochromic 3719-3759Crossref With respect early were primarily restricted (<400 nm), damaging difficult distinguish among due universal absorption. efforts unveiled numerous light-activated derivatives, leverage inexpensive mild LEDs narrow-band sources. Stilbenes (1945),31Waldeck D.H. dynamics stilbenes.Chem. 1991; 91: 415-436Crossref (1101) azobenzenes (1937),12Hartley ?-bisimines (2014),32Greb Lehn J.-M. Light-driven motors: imines four-step two-step unidirectional rotors.J. 136: 13114-13117Crossref (158) (thio)indigo (1961),33Izmail’skii V.A. Mostoslavskii Absorption spectra 3- oxo-2,3-dihydrothianaphthene derivatives. II. Isomerism 2- benzylidene-3-oxo-2,3-dihydrothionaphthene.Ukr. Khem. Zh. 1961; : 234-237Google hydrazones (2009) Z/E light.34Harris J.D. Moran Aprahamian I. architectures.Proc. Natl. Acad. U S 115: 9414-9422Crossref discovered 1937 since blossomed array derivatives UV-to-visible (300–700 rapid photochromism, changes, resistance (cycling stability), motion. These briefly below, highlighting windows them synthesized 1843,35Laurent Mémoire sur la série stilbique [Memoir stilbene series].Comptes Rendus. 1843; 16: 856Google until 1945 4A ).31Waldeck Traditional non-functionalized strictly absorb light, peak 294 nm E-stilbene 278 Z-stilbene.36Suzuki spatial configurations ultraviolet derivatives.Bull. Jpn. 1952; 25: 145-150Crossref Z isomer results Z-to-E cyclization form dihydrophenanthrene, photocyclization/-reversion. Cyclization avoided fused analog (stiff-stilbene),37Oelgemöller Frank R. Lemmen Lenoir Lex Inoue Synthesis, structural cyclic stilbenes.Tetrahedron. 68: 4048-4056Crossref (9) adopted motif Feringa-type motors.38van Leeuwen Lubbe Štacko Wezenberg S.J. Dynamic motors.Nat. 1: 0096Crossref Scholar,39Kassem van Wilson M.R. Leigh D.A. Artificial motors.Chem. 46: 2592-2621Crossref Azobenzenes, reported 1937,12Hartley most widely studied family ease versatility. They follow process similar stilbenes, presence nitrogen notable dipole moment red-shift relative analogous stilbene. Irradiation bare azobenzene (?340 converts thermodynamically stable E less form, reverts blue (?450 4B).40Beharry A.A. Woolley G.A. Azobenzene phwotoswitches biomolecules.Chem. 40: 4422Crossref discovery, impressive library examined terms switching kinetics, thermal stability, absorption.41Dong Babalhavaeji Samanta Beharry Red-shifting vivo use.Acc. Res. 2662-2670Crossref (314) Introducing electron-donating amine withdrawing nitro groups opposing para positions generates “push-pull” ?120 isomers.42Kobayashi Yokoyama Kamei Substituent solvent push-pull-substituted cis-azobenzenes.Chem. 1987; 138: 333-338Crossref (36) Azobenzenes ortho-fluorination addressed providing high photoconversion remarkably half-lives photostationary configuration.43Bléger Schwarz Brouwer A.M. Hecht o-fluoroazobenzenes readily nearly quantitative two-way light.J. 134: 20597-20600Crossref (421) Scholar,44Knie Utecht Zhao Kulla Kovalenko Saalfrank Bléger ortho-Fluoroazobenzenes: switches very long-lived isomers.Chem. Eur. 20: 16492-16501Crossref (179) Coordination BF2 proved effective method 710 (far-red) isomer.45Yang Hughes Near-infrared azo-BF 2 switches.J. 13190-13193Crossref (122) Scholar,46Yang -coordinated compound.J. 15221-15224Crossref (153) Thus, functionalized represent excellent candidates photochemistry. ?-Bisimines, Jean-Marie 2014,32Greb photochemical/thermal configurations, (Z,Z), (E,Z), (E,E), rotation around C=N double bonds 4C). ?-Bisimines employed machines. (Z,Z) (E,E) <280 (E,Z) 365 nm, thermally. limits presents opportunity novel ?-bisimine derivatives.47Greb Eichhöfer Internal C-C bond photoisomers ?-bisimines: light-responsive regulator imine photoswitching.Eur. Org. 2016: 1243-1246Crossref Indigo 1961 4D),33Izmail’skii low-energy photostability. example, hemiindigo (X = N, Figure 4D) electron-rich aromatic substituents photoswitched yellow-to-red (?593–633 isomers. advantageous photopharmacological biological applications, poor stability limiting. end, N-aryl functionalization incorporation electron-withdrawing CF3 CN) enhance maintaining red light.48Huang C.-Y. Bonasera Hristov Garmshausen Schmidt B.M. N,N?-Disubstituted indigos available red-light half-lives.J. 15205-15211Crossref (43) (Acyl)Hydrazones photoswitch, Lehn's group 2011 4E).49Chaur M.N. Collado Configurational constitutional information storage: systems pyridyl acyl hydrazones.Chem. 17: 248-258Crossref negative (photoinduced decoloration coloration), large (for isomers), half-life, good yields favorable properties. Additionally, hydrazone phenyl quinolinyl retain photoswitchability polar protic solvents, aprotic acids bases. 2015, coworkers syn
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ژورنال
عنوان ژورنال: Matter
سال: 2021
ISSN: ['2604-7551']
DOI: https://doi.org/10.1016/j.matt.2021.03.021