Circularly polarized luminescence based on small organic fluorophores

Materials Today Chemistry - Tập 23 - Trang 100651 - 2022
Y. Chen1,2
1Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China
2University of Chinese Academy of Sciences, Beijing 100190, China

Tài liệu tham khảo

Yang, 2013, Circularly polarized light detection by a chiral organic semiconductor transistor, Nat. Photonics, 7, 634, 10.1038/nphoton.2013.176 Heffern, 2014, Lanthanide probes for bioresponsive imaging, Chem. Rev., 114, 4496, 10.1021/cr400477t Maeda, 2013, Recent progress in research on stimuli-responsive circularly polarized luminescence based on π-conjugated molecules, Pure Appl. Chem., 85, 1967, 10.1351/pac-con-12-11-09 Longhi, 2016, Circularly polarized luminescence: a review of experimental and theoretical aspects, Chirality, 28, 696, 10.1002/chir.22647 Zinna, 2015, Lanthanide circularly polarized luminescence: bases and applications, Chirality, 27, 1, 10.1002/chir.22382 Han, 2018, Recent progress on circularly polarized luminescent materials for organic optoelectronic devices, Adv. Opt. Mater., 6, 1800538, 10.1002/adom.201800538 Grell, 2001, A compact device for the efficient, electrically driven generation of highly circularly polarized light, Adv. Mater., 13, 577, 10.1002/1521-4095(200104)13:8<577::AID-ADMA577>3.0.CO;2-K Jeong, 2007, Highly circularly polarized electroluminescence from organic light-emitting diodes with wide-band reflective polymeric cholesteric liquid crystal films, Appl. Phys. Lett., 90, 211106, 10.1063/1.2741603 Pope, 1991, Polyoxometalate chemistry: an old field with new dimensions in several disciplines, Angew. Chem. Int. Ed. Engl., 30, 34, 10.1002/anie.199100341 Coronado, 1998, Polyoxometalate-based molecular materials, Chem. Rev., 98, 273, 10.1021/cr970471c Gómez-Romero, 1997, Hybrid organic-inorganic electrodes: the molecular material formed between polypyrrole and the phosphomolybdate anion, Adv. Mater., 9, 144, 10.1002/adma.19970090210 Kulkarni, 2019, Molecular design principles for achieving strong chiroptical properties of fluorene copolymers in thin films, Chem. Mater., 31, 6633, 10.1021/acs.chemmater.9b00601 Ikai, 2018, Chiral amplification in π-conjugated helical polymers with circularly polarized luminescence, Macromolecules, 51, 2328, 10.1021/acs.macromol.8b00229 Meng, 2017, Circularly polarized luminescence based chirality transfer of the chiral BINOL moiety via rigid π-conjugation chain backbone structures, Polym. Chem., 8, 1555, 10.1039/C6PY02218A Zhao, 2018, Intense circularly polarized luminescence contributed by helical chirality of monosubstituted polyacetylenes, Macromolecules, 51, 7104, 10.1021/acs.macromol.8b01545 Han, 2017, Amplification of circularly polarized luminescence through triplet–triplet annihilation-based photon upconversion, J. Am. Chem. Soc., 139, 9783, 10.1021/jacs.7b04611 Sawada, 2012, Rhodium-catalyzed enantioselective synthesis, crystal structures, and photophysical properties of helically chiral 1,1’-bitriphenylenes, J. Am. Chem. Soc., 134, 4080, 10.1021/ja300278e Goto, 2012, Intermolecular oxidative annulation of 2-aminoanthracenes to diazaacenes and aza[7]helicenes, Angew. Chem. Int. Ed., 51, 10333, 10.1002/anie.201204863 Jin, 2019, Optically active upconverting nanoparticles with induced circularly polarized luminescence and enantioselectively triggered photopolymerization, ACS Nano, 13, 2804, 10.1021/acsnano.8b08273 Wang, 2019, Inversion of circularly polarized luminescence of nanofibrous hydrogels through coassembly with achiral coumarin derivatives, ACS Nano, 13, 7281, 10.1021/acsnano.9b03255 Zhang, 2019, Real-time monitoring of hierarchical self-assembly and induction of circularly polarized luminescence from achiral luminogens, ACS Nano, 13, 3618, 10.1021/acsnano.9b00218 Lunkley, 2008, Extraordinary circularly polarized luminescence activity exhibited by cesium tetrakis(3-heptafluoro-butylryl-(+)-camphorato) Eu(III) complexes in EtOH and CHCl3 solutions, J. Am. Chem. Soc., 130, 13814, 10.1021/ja805681w Han, 2017, Circularly polarized phosphorescent electroluminescence from chiral cationic iridium(III) isocyanide complexes, Adv. Opt. Mater., 5, 1700359, 10.1002/adom.201700359 Zinna, 2017, Design of lanthanide-based OLEDs with remarkable circularly polarized electroluminescence, Adv. Funct. Mater., 27, 1603719, 10.1002/adfm.201603719 Ayers, 2020, Circularly polarized luminescence from enantiopure C2-symmetrical tetrakis(2-pyridylmethyl)-1,2-diaminocyclohexane lanthanide complexes, Inorg. Chem., 59, 7657, 10.1021/acs.inorgchem.0c00628 Zinna, 2015, Highly circularly polarized electroluminescence from a chiral europium complex, Adv. Mater., 27, 1791, 10.1002/adma.201404891 Kumar, 2015, Circularly polarized luminescence in chiral molecules and supramolecular assemblies, J. Phys. Chem. Lett., 6, 3445, 10.1021/acs.jpclett.5b01452 Sanchez-Carnerero, 2015, Circularly polarized luminescence from simple organic molecules, Chem. Eur J., 21, 13488, 10.1002/chem.201501178 Kumar, 2013, Circularly polarized luminescence in supramolecular assemblies of chiral bichromophoric perylene bisimides, Chem. Eur J., 19, 14090, 10.1002/chem.201302146 Gon, 2016, Synthesis of optically active, X-shaped, conjugated compounds and dendrimers based on planar chiral [2.2]paracyclophane, leading to highly emissive circularly polarized luminescence, Chem. Eur J., 22, 2291, 10.1002/chem.201504270 Nishimura, 2017, Oxygen-bridged diphenylnaphthylamine as a scaffold for full-color circularly polarized luminescent materials, J. Org. Chem., 82, 5242, 10.1021/acs.joc.7b00511 Katayama, 2016, Two-step synthesis of boron-fused double helicenes, J. Am. Chem. Soc., 138, 5210, 10.1021/jacs.6b01674 Saikawa, 2016, Synthesis of figure-of-eight helical bisBODIPY macrocycles and their chiroptical properties, Chem. Commun., 52, 10727, 10.1039/C6CC05439K Otani, 2017, Facile two-step synthesis of 1,10-phenanthroline-derived polyaza[7]helicenes with high fluorescence and CPL efficiency, Angew. Chem. Int. Ed., 56, 3906, 10.1002/anie.201700507 Brandt, 2016, Circularly polarized phosphorescent electroluminescence with a high dissymmetry factor from PHOLEDs based on a platinahelicene, J. Am. Chem. Soc., 138, 9743, 10.1021/jacs.6b02463 Feuillastre, 2016, Design and synthesis of new circularly polarized thermally activated delayed fluorescence emitters, J. Am. Chem. Soc., 138, 3990, 10.1021/jacs.6b00850 Schulz, 2017, Organic photodiodes from homochiral L-proline derived squaraine compounds with strong circular dichroism, Phys. Chem. Chem. Phys., 19, 6996, 10.1039/C7CP00306D Josse, 2017, Enantiopure versus racemic naphthalimide end-capped helicenic non-fullerene electron acceptors: impact on organic photovoltaics performance, Chem. Eur J., 23, 6277, 10.1002/chem.201701066 Brandt, 2017, The added value of small-molecule chirality in technological applications, Nat. Rev. Chem., 1, 10.1038/s41570-017-0045 Riehl, 1986, Circularly polarized luminescence spectroscopy, Chem. Rev., 86, 1, 10.1021/cr00071a001 Shen, 2012, Helicenes: synthesis and applications, Chem. Rev., 112, 1463, 10.1021/cr200087r Zhao, 2019, Advances in helicene derivatives with circularly polarized luminescence, Chem. Commun., 55, 13793, 10.1039/C9CC06861A Chen, 2017, Closed pentaaza[9]helicene and hexathia[9]/[5]helicene: oxidative fusion reactions of ortho-phenylene-bridged cyclic hexapyrroles and hexathiophenes, Angew. Chem. Int. Ed., 56, 14688, 10.1002/anie.201708429 Labrador, 2019, Stereochemical significance of O to N atom interchanges within cationic helicenes: experimental and computational evidence of near racemization to remarkable enantiospecificity, Chem. Sci., 10, 7059, 10.1039/C9SC02127B Domínguez, 2018, Azabora[5]helicene charge-transfer dyes show efficient and spectrally variable circularly polarized luminescence, Chem. Eur J., 24, 12660, 10.1002/chem.201801908 Uematsu, 2018, Synthesis and properties of [7]helicene and [7]helicene-like compounds with a cyclopenta[1,2-b:4,3-b’]dithiophene or dithieno[2,3-b:3’,2’-d]heterole skeleton, Phys. Chem. Chem. Phys., 20, 3286, 10.1039/C7CP06342C Cruz, 2018, Undecabenzo[7]superhelicene: a helical nanographene ribbon as a circularly polarized luminescence emitter, Angew. Chem. Int. Ed., 57, 14782, 10.1002/anie.201808178 Nakakuki, 2018, Matsuda, Synthesis of a helical analogue of kekulene: a flexible π-expanded helicene with large helical diameter acting as a soft molecular spring, J. Am. Chem. Soc., 140, 15461, 10.1021/jacs.8b09825 Maeda, 2019, Synthesis of chiral carbazole-based BODIPYs showing circularly polarized luminescence, Chem. Commun., 55, 3136, 10.1039/C9CC00894B Maeda, 2020, Synthesis and chiroptical properties of chiral carbazole-based BODIPYs, Chem. Eur J., 26, 4261, 10.1002/chem.201904954 Clarke, 2017, Circularly polarised luminescence from helically chiral “confused” N, N, O, C-boron-chelated dipyrromethenes (BODIPYs), ChemPhotoChem, 1, 513, 10.1002/cptc.201700106 Jimenez, 2017, Chiral organic dyes endowed with circularly polarized laser emission, J. Phys. Chem. C, 121, 5287, 10.1021/acs.jpcc.7b00654 Meng, 2017, Reversal aggregation-induced circular dichroism from axial chirality transfer via self-assembled helical nanowires, RSC Adv., 7, 15851, 10.1039/C7RA00703E Sánchez-Carnerero, 2014, Circularly polarized luminescence by visible-light absorption in a chiral O-BODIPY dye: unprecedented design of CPL organic molecules from achiral chromophores, J. Am. Chem. Soc., 136, 3346, 10.1021/ja412294s Jimenez, 2019, Modulating ICT emission: a new strategy to manipulate the CPL sign in chiral emitters, Chem. Commun., 55, 1631, 10.1039/C8CC09401B Maeda, 2020, Azahelicene-fused BODIPY analogues showing circularly polarized luminescence, Angew. Chem. Int. Ed., 59, 7813, 10.1002/anie.202001186 Maeda, 2020, Aggregation-induced circularly polarized luminescence from boron complexes with a carbazolyl schiff base, Chem. Eur J., 26, 13016, 10.1002/chem.202001463 Longhi, 2013, Experimental and calculated CPL spectra and related spectroscopic data of camphor and other simple chiral bicyclic ketones, Chirality, 25, 589, 10.1002/chir.22176 Castiglion, 2012, Ultraviolet, circular dichroism, fluorescence, and circularly polarized luminescence spectra of regioregular poly-[3-((s)-2-methylbutyl)-thiophene] in solution, Chirality, 24, 725, 10.1002/chir.22023 Dhbaibi, 2018, Exciton coupling in diketopyrrolopyrrole–helicene derivatives leads to red and near-infrared circularly polarized luminescence, Chem. Sci., 9, 735, 10.1039/C7SC04312K Feng, 2018, Design of multi-functional AIEgens: tunable emission, circularly polarized luminescence and self-assembly by dark through-bond energy transfer, J. Mater. Chem. C, 6, 8934, 10.1039/C8TC02504E Li, 2017, Fabrication of circular polarized luminescent helical fibers from chiral phenanthro[9,10]imidazole derivatives, Mater. Chem. Front., 1, 646, 10.1039/C6QM00120C Inouye, 2014, A doubly alkynylpyrene-threaded [4]rotaxane that exhibits strong circularly polarized luminescence from the spatially restricted excimer, Angew. Chem. Int. Ed., 53, 14392, 10.1002/anie.201408193 Nakabayashi, 2014, Nonclassical dual control of circularly polarized luminescence modes of binaphthyl–pyrene organic fluorophores in fluidic and glassy media, Chem. Commun., 50, 13228, 10.1039/C4CC02946A Takaishi, 2017, Helical oligonaphthodioxepins showing intense circularly polarized luminescence (CPL) in solution and in the solid state, Chem. Eur J., 23, 9249, 10.1002/chem.201702143 Takaishi, 2011, Helical chirality of azobenzenes induced by an intramolecular chiral axis and potential as chiroptical switches, Chem. Eur J., 17, 1778, 10.1002/chem.201003087 Takaishi, 2010, Multibridged chiral naphthalene oligomers with continuous extreme-cisoid conformation, Org. Lett., 12, 1832, 10.1021/ol100582v Sue, 2009, Synthesis of chiral dotriacontanaphthalenes: how many naphthalene units are we able to elaborately connect?, J. Org. Chem., 74, 3940, 10.1021/jo900463t Takaishi, 2018, Intense excimer CPL of pyrenes linked to a quaternaphthyl, Chem. Commun., 54, 1449, 10.1039/C7CC09187G Takaishi, 2019, Evolving fluorophores into circularly polarized luminophores with a chiral naphthalene tetramer: proposal of excimer chirality rule for circularly polarized luminescence, J. Am. Chem. Soc., 141, 6185, 10.1021/jacs.9b02582 Inoue, 2018, Hash-mark-shaped azaacene tetramers with axial chirality, J. Am. Chem. Soc., 140, 7152, 10.1021/jacs.8b02689 Chen, 2020, Planar chiral organoboranes with thermoresponsive emission and circularly polarized luminescence: integration of pillar[5]arenes with boron chemistry, Angew. Chem. Int. Ed., 59, 11267, 10.1002/anie.202001145 Ogoshi, 2016, Pillarn-shaped macrocyclic hosts pillar[n]arenes: new key players for supramolecular chemistry, Chem. Rev., 116, 7937, 10.1021/acs.chemrev.5b00765 Li, 2018, Tetraphenylethylene-interweaving conjugated macrocycle polymer materials as two-photon fluorescence sensors for metal ions and organic molecules, Adv. Mater., 30, 1800177, 10.1002/adma.201800177 Takaishi, 2020, Solvent-induced sign inversion of circularly polarized luminescence: control of excimer chirality by hydrogen bonding, J. Am. Chem. Soc., 142, 1774, 10.1021/jacs.9b13184 Aggeli, 2001, Hierarchical self-assembly of chiral rod-like molecules as a model for peptide β-sheet tapes, ribbons, fibrils, and fibers, Proc. Natl. Acad. Sci. U. S. A., 98, 11857, 10.1073/pnas.191250198 Ajayaghosh, 2006, Transcription and amplification of molecular chirality to oppositely biased supramolecular π helices, Angew. Chem. Int. Ed., 45, 1141, 10.1002/anie.200503142 Guo, 2004, Chiroptical transcription of helical information through supramolecular harmonization with dynamic helices, J. Am. Chem. Soc., 126, 716, 10.1021/ja039369p Liang, 2020, Hierarchically chiral lattice self-assembly induced circularly polarized luminescence, ACS Nano, 14, 3190, 10.1021/acsnano.9b08408 Yang, 2017, Chirality and energy transfer amplified circularly polarized luminescence in composite nanohelix, Nat. Commun., 8, 15727, 10.1038/ncomms15727 Han, 2017, Full-color tunable circularly polarized luminescent nanoassemblies of achiral AIEgens in confined chiral nanotubes, Adv. Mater., 29, 1606503, 10.1002/adma.201606503 Goto, 2017, Induction of strong and tunable circularly polarized luminescence of nonchiral, nonmetal, low-molecular-weight fluorophores using chiral nanotemplates, Angew. Chem. Int. Ed., 56, 2989, 10.1002/anie.201612331 Oishi, 2020, Polymer encapsulation and stabilization of molecular gel-based chiroptical information for strong, tunable circularly polarized luminescence film, J. Mater. Chem. C, 8, 8732, 10.1039/D0TC01480J Li, 2019, Stoichiometry-controlled inversion of circularly polarized luminescence in co-assembly of chiral gelators with an achiral tetraphenylethylene derivative, Chem. Commun., 55, 2194, 10.1039/C8CC08924H Zhao, 2019, Combining chiral helical polymer with achiral luminophores for generating full-color, on−off, and switchable circularly polarized luminescence, Macromolecules, 52, 376, 10.1021/acs.macromol.8b02305 Zhao, 2020, Multifarious chiral nanoarchitectures serving as handed-selective fluorescence filters for generating full-color circularly polarized luminescence, ACS Nano, 14, 3208, 10.1021/acsnano.9b08618 Zhao, 2020, Color-tunable circularly polarized luminescence with helical polyacetylenes as fluorescence converters, Adv. Optical Mater., 8, 2000858, 10.1002/adom.202000858 Okayasu, 2018, Evaluation of circularly polarized luminescence in a chiral lanthanide ensemble, Mol. Syst. Des. Eng., 3, 66, 10.1039/C7ME00082K Shi, 2020, Circularly polarized luminescence from semiconductor quantum rods templated by self-assembled cellulose nanocrystals, J. Mater. Chem. C, 8, 1048, 10.1039/C9TC05751J Deng, 2020, High circularly polarized luminescence brightness from analogues of Shibasaki's lanthanide complexes, Chem. Commun., 56, 14813, 10.1039/D0CC06568D Li, 2021, AIE-active chiral [3]rotaxanes with switchable circularly polarized luminescence, Angew. Chem. Int. Ed., 60, 9507, 10.1002/anie.202100934 Cerdán, 2017, Circularly polarized laser emission in optically active organic dye solutions, Phys. Chem. Chem. Phys., 19, 22088, 10.1039/C7CP03303F Song, 2020, Circularly polarized luminescence from AIEgens, J. Mater. Chem. C, 8, 3284, 10.1039/C9TC07022B He, 2021, Improved enantioselectivity in thiol–ene photopolymerization of sulphur-containing polymers with circularly polarized luminescence, Polym. Chem., 12, 2433, 10.1039/D1PY00082A Scanga, 2021, Helical polymer self-assembly and chiral nanostructure formation, Polym. Chem., 12, 1857, 10.1039/D0PY01558J Ni, 2021, Circularly polarized luminescence from structurally coloured polymer films, Chem. Commun., 57, 2796, 10.1039/D1CC00201E Yang, 2019, Photon-upconverting chiral liquid crystal: significantly amplified upconverted circularly polarized luminescence, Chem. Sci., 10, 172, 10.1039/C8SC03806F Park, 2019, Amplified circularly polarized phosphorescence from co-assemblies of platinum(II) complexes, Chem. Sci., 10, 1294, 10.1039/C8SC04509G Starck, 2019, Excitation modulation of Eu:BPEPC based complexes as low-energy reference standards for circularly polarised luminescence (CPL), Chem. Commun., 55, 14115, 10.1039/C9CC07290J Jiang, 2019, Helical nanostructures: chirality transfer and a photodriven transformation from superhelix to nanokebab, Angew. Chem. Int. Ed., 58, 785, 10.1002/anie.201811060 Liu, 2019, Water inversed helicity of nanostructures from ionic self-assembly of a chiral gelator and an achiral component, Soft Matter, 15, 6557, 10.1039/C9SM01176E Anetai, 2018, Circular polarized luminescence of hydrogen-bonded molecular assemblies of chiral pyrene derivatives, J. Phys. Chem. C, 122, 6323, 10.1021/acs.jpcc.7b12747 Wang, 2018, Helix induction to polyfluorenes using circularly polarized light: chirality amplification, phase-selective induction, and anisotropic emission, Macromolecules, 51, 6865, 10.1021/acs.macromol.8b01453 Zhao, 2020, New perspectives to trigger and modulate circularly polarized luminescence of complex and aggregated systems: energy transfer, photon upconversion, charge transfer, and qrganic radical, Acc. Chem. Res., 53, 1279, 10.1021/acs.accounts.0c00112 Zhao, 2020, Amplifying dissymmetry factor of upconverted circularly polarized luminescence through chirality-induced spin polarization in the photon upconversion process, J. Phys. Chem. Lett., 11, 311, 10.1021/acs.jpclett.9b03408 Song, 2018, Highly efficient circularly polarized electroluminescence from aggregation-induced emission luminogens with amplified chirality and delayed fluorescence, Adv. Funct. Mater., 28, 1800051, 10.1002/adfm.201800051 Zhang, 2021, Improving the overall properties of circularly polarized luminescent materials through arene–perfluoroarene interactions, Angew. Chem. Int. Ed., 60, 4575, 10.1002/anie.202014891 Pan, 2021, Two chirality transfer channels assist handedness inversion and amplification of circularly polarized luminescence in chiral helical polyacetylene thin films, Macromolecules, 54, 5043, 10.1021/acs.macromol.1c00563