Photoinduced reversible phase transition in a phenothiazine-based metal-organic framework

Rice, 2020, Photophysics modulation in photoswitchable metal–organic frameworks, Chem. Rev., 120, 8790, 10.1021/acs.chemrev.9b00350 Liu, 2020, Stimuli-responsive structural changes in metal–organic frameworks, Chem. Commun., 56, 9416, 10.1039/D0CC03197F Drake, 2022, Light-induced switchable adsorption in azobenzene- and stilbene-based porous materials, Trends Chem., 4, 32, 10.1016/j.trechm.2021.11.003 Danowski, 2021, Photoresponsive porous materials, Nanoscale Adv., 3, 24, 10.1039/D0NA00647E Park, 2015, Photochromic metal–organic frameworks: reversible control of singlet oxygen generation, Angew. Chem. Int. Ed. Engl., 54, 430, 10.1002/anie.201408862 Mondal, 2017, Reversible multistimuli switching of a spiropyran-functionalized organic cage in solid and solution, J. Org. Chem., 82, 7783, 10.1021/acs.joc.7b00722 Dolgopolova, 2017, Multifaceted modularity: a key for stepwise building of hierarchical complexity in actinide metal–organic frameworks, J. Am. Chem. Soc., 139, 16852, 10.1021/jacs.7b09496 Dolgopolova, 2019, Connecting wires: photoinduced electronic structure modulation in metal–organic frameworks, J. Am. Chem. Soc., 141, 5350, 10.1021/jacs.8b13853 Dolgopolova, 2017, A metal–organic framework as a flask: photophysics of confined chromophores with a benzylidene imidazolinone core, Chem. Commun., 53, 7361, 10.1039/C7CC02253K Williams, 2018, Flipping the switch: fast photoisomerization in a confined environment, J. Am. Chem. Soc., 140, 7611, 10.1021/jacs.8b02994 Kim, 2012, Postsynthetic ligand exchange as a route to functionalization of metal-organic frameworks, Chem. Sci., 3, 126, 10.1039/C1SC00394A Li, 2016, A robust metal-organic framework for dynamic light-induced swing adsorption of Carbon dioxide, Chemistry, 22, 11176, 10.1002/chem.201602671 Li, 2016, MaLISA - a cooperative method to release adsorbed gases from metal-organic frameworks, J. Mater. Chem., 4, 18757, 10.1039/C6TA09826F Li, 2016, Magnetic metal-organic frameworks for efficient Carbon dioxide capture and remote trigger release, Adv. Mater., 28, 1839, 10.1002/adma.201505320 Li, 2019, Loading photochromic molecules into a luminescent metal–organic framework for information anticounterfeiting, Angew. Chem. Int. Ed. Engl., 58, 18025, 10.1002/anie.201910467 Müller, 2017, Photoswitchable nanoporous films by loading azobenzene in metal-organic frameworks of type HKUST-1, Chem. Commun., 53, 8070, 10.1039/C7CC00961E Garg, 2019, Conductance photoswitching of metal–organic frameworks with embedded spiropyran, Angew. Chem. Int. Ed. Engl., 58, 1193, 10.1002/anie.201811458 Heinke, 2014, Photoswitching in two-component surface-mounted metal–organic frameworks: optically triggered release from a molecular container, ACS Nano, 8, 1463, 10.1021/nn405469g Kanj, 2019, Switching the enantioselectivity of nanoporous host materials by light, Chem. Commun., 55, 8776, 10.1039/C9CC02849H Müller, 2017, Switching thin films of azobenzene-containing metal–organic frameworks with visible light, Chemistry, 23, 5434, 10.1002/chem.201700989 Schwartz, 2018, Smart nanoporous metal–organic frameworks by embedding photochromic molecules – state of the art and future perspectives, Photochem. Photobiol. Sci., 17, 864, 10.1039/c7pp00456g Wang, 2018, Series of photoswitchable azobenzene-containing metal–organic frameworks with variable adsorption switching effect, J. Phys. Chem. C, 122, 19044, 10.1021/acs.jpcc.8b05843 Lo, 2020, Rapid desolvation-triggered domino lattice rearrangement in a metal–organic framework, Nat. Chem., 12, 90, 10.1038/s41557-019-0364-0 Zheng, 2017, Flexible interlocked porous frameworks allow quantitative photoisomerization in a crystalline solid, Nat. Commun., 8, 100, 10.1038/s41467-017-00122-5 Chen, 2022, Direct observation of modulated radical spin states in metal–organic frameworks by controlled flexibility, J. Am. Chem. Soc., 144, 2685, 10.1021/jacs.1c11417 Sun, 2004, Donor-acceptor (electronic) coupling in the precursor complex to organic electron transfer: intermolecular and intramolecular self-exchange between phenothiazine redox centers, J. Am. Chem. Soc., 126, 1388, 10.1021/ja038746v Ronzani, 2013, Comparison of the photophysical properties of three phenothiazine derivatives: transient detection and singlet oxygen production, Photochem. Photobiol. Sci., 12, 2160, 10.1039/c3pp50246e Christensen, 2018, Phenothiazine radical cation excited states as super-oxidants for energy-demanding reactions, J. Am. Chem. Soc., 140, 5290, 10.1021/jacs.8b01778 Freitas, 2014, Structural, energetic and reactivity properties of phenoxazine and phenothiazine, J. Chem. Therm., 73, 110, 10.1016/j.jct.2013.11.013 Fang, 2018, Investigating subcellular compartment targeting effect of porous coordination cages for enhancing cancer nanotherapy, Small, 14, e1802709, 10.1002/smll.201802709 Franz, 2008, Synthesis and electronic properties of sterically demanding N-arylphenothiazines and unexpected buchwald-Hartwig aminations, J. Org. Chem., 73, 1795, 10.1021/jo702389v Rupérez, 1984, EPR study of the phenothiazine cation radical, Spectrochim. Acta Mol. Spectros, 40, 1021, 10.1016/0584-8539(84)80129-4 Bodea, 1968, Recent advances in the chemistry of phenothiazines, Adv. Heterocycl. Chem., 9, 321, 10.1016/S0065-2725(08)60375-X Beckett, 1978, Aromatic oxidation of some phenothiazines, Xenobiotica, 8, 721, 10.3109/00498257809069585 Abdallah, 2019, Phenothiazine derivatives as photoredox catalysts for cationic and radical photosensitive resins for 3D printing technology and photocomposite synthesis, Polym. Chem., 10, 6145, 10.1039/C9PY01265F Gu, 2019, Design and control of gas diffusion process in a nanoporous soft crystal, Science, 363, 387, 10.1126/science.aar6833 Quddus, 2014, Oxygen mediated synthesis of high quality InN nanowires above their decomposition temperature, Nanoscale, 6, 1166, 10.1039/C3NR03991A Blatov, 2014, Applied topological analysis of crystal structures with the program package ToposPro, Cryst. Growth Des., 14, 3576, 10.1021/cg500498k Nelson, 2009, Supercritical processing as a route to high internal surface areas and permanent microporosity in Metal−Organic framework materials, J. Am. Chem. Soc., 131, 458, 10.1021/ja808853q Kaur, 2021, Review on flexible metal-organic frameworks, ChemistrySelect, 6, 8227, 10.1002/slct.202101524 Thommes, 2015, Physisorption of gases, with special reference to the evaluation of surface area and pore size distribution (IUPAC Technical Report), Pure Appl. Chem., 87, 1051, 10.1515/pac-2014-1117 Drake, 2022, Influence of metal identity on light-induced switchable adsorption in azobenzene-based metal–organic frameworks, ACS Appl. Mater. Interfaces, 14, 11192, 10.1021/acsami.1c18266 Kamat, 1981, Photoinduced electron-ejection from methylene blue in water and acetonitrile, J. Phys. Chem., 85, 3864, 10.1021/j150625a031 Kayser, 1976, The photoreduction of methylene blue by amines I. a flash photolysis study of the reaction between triplet methylene blue and amines, Photochem. Photobiol., 24, 395, 10.1111/j.1751-1097.1976.tb06845.x Shine, 1965, Ion radicals. V. Phenothiazine, phenothiazine 5-oxide, and phenothiazone-3 in acid Solutions1, 2, J. Org. Chem., 30, 2130, 10.1021/jo01018a004 Spek, 2015, PLATON SQUEEZE: a tool for the calculation of the disordered solvent contribution to the calculated structure factors, Acta Crystallogr. C Struct. Chem., 71, 9, 10.1107/S2053229614024929 Yao, 2014, Molecular motor-driven abrupt anisotropic shape change in a single crystal of a Ni complex, Nat. Chem., 6, 1079, 10.1038/nchem.2092 Naumov, 2015, Mechanically responsive molecular crystals, Chem. Rev., 115, 12440, 10.1021/acs.chemrev.5b00398 Tricarico, 2022, Mechanical properties and nanostructure of monolithic zeolitic imidazolate frameworks: a nanoindentation, nanospectroscopy and finite-element study, Mater. Today Nano, 17, 100166, 10.1016/j.mtnano.2021.100166 Burtch, 2018, Mechanical properties in metal–organic frameworks: emerging opportunities and challenges for device functionality and technological applications, Adv. Mater., 30, 1704124, 10.1002/adma.201704124 Redfern, 2019, Mechanical properties of metal–organic frameworks, Chem. Sci., 10, 10666, 10.1039/C9SC04249K Drake, 2021, Thermal decarboxylation for the generation of hierarchical porosity in isostructural metal–organic frameworks containing open metal sites, Mater. Adv., 2, 5487, 10.1039/D1MA00163A Campillo-Alvarado, 2019, Exploiting boron coordination: B←N bond supports a [2+2] photodimerization in the solid state and generation of a diboron bis-tweezer for benzene/thiophene separation, Angew. Chem. Int. Ed. Engl., 58, 5413, 10.1002/anie.201812174 Moreno-Piraján, 2020, Heat of adsorption: a comparative study between the experimental determination and theoretical models using the system CH4-MOFs, J. Chem. Eng. Data, 65, 3130, 10.1021/acs.jced.0c00159 Langmuir, 1918, The adsorption of gases on plane surfaces of glass, mica and platinum, J. Am. Chem. Soc., 40, 1361, 10.1021/ja02242a004 Cai, 2021, Photoinduced electron-transfer (PIET) strategy for selective adsorption of CO2 over C2H2 in a MOF, Angew. Chem. Int. Ed. Engl., 60, 18223, 10.1002/anie.202105491 Vázquez, 1992, Determination of the molar absorptivities of phenothiazine cation radicals generated by oxidation with hydrogen peroxide/peroxidase, Anal. Biochem., 202, 245, 10.1016/0003-2697(92)90101-C Martin, 2022, Stimuli-modulated metal oxidation states in photochromic MOFs, J. Am. Chem. Soc., 144, 4457, 10.1021/jacs.1c11984 Conti, 2021, Examining the effect of dopant ionic radius on plasmonic M:ZnO nanocrystals (M = Al3+, Ga3+, In3+), J. Phys. Chem. C, 125, 7772, 10.1021/acs.jpcc.1c00529 Conti, 2020, Carrier density, effective mass, and nuclear relaxation pathways in plasmonic Sn:In2O3 nanocrystals, J. Phys. Chem. C, 124, 28220, 10.1021/acs.jpcc.0c09448 Kays, 2021, Controlled synthesis and exploration of CuxFeS4 bornite nanocrystals, Chem. Mater., 33, 7408, 10.1021/acs.chemmater.1c02029 Connelly, 1996, Chemical redox agents for organometallic chemistry, Chem. Rev., 96, 877, 10.1021/cr940053x Araujo, 2021, Tunable band-edge potentials and charge storage in colloidal tin-doped indium oxide (ITO) nanocrystals, ACS Nano, 15, 14116, 10.1021/acsnano.1c04660