Circularly polarized luminescence based on small organic fluorophores
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