A solid-state emissive and solvatofluorochromic fluorophore and its application in high-contrast, fast, and repeatable thermochromic blends

Dyes and Pigments - Tập 163 - Trang 412-419 - 2019
Binhong Yu1, Danyang Liu1, Yi Wang1, Ting Zhang1, Yu-Mo Zhang2, Minjie Li1, Sean Xiao-An Zhang1
1State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, 130012, PR China
2College of Chemistry, Jilin University, Changchun 130012, PR China

Tài liệu tham khảo

Hinoue, 2012, Regulation of π-stacked anthracene arrangement for fluorescence modulation of organic solid from monomer to excited oligomer emission, Chem Eur J, 18, 4634, 10.1002/chem.201103518 Li, 2009, Functionalized siloles: versatile synthesis, aggregation-induced emission, and sensory and device applications, Adv Funct Mater, 19, 905, 10.1002/adfm.200801278 Wang, 2015, Full-color tunable mechanofluorochromism and excitation-dependent emissions of single-arm extended tetraphenylethylenes, J Mater Chem C, 3, 12328, 10.1039/C5TC02623G Qin, 2012, Biocompatible nanoparticles with aggregation-induced emission characteristics as far-red/near-infrared fluorescent bioprobes for in vitro and in vivo imaging applications, Adv Funct Mater, 22, 771, 10.1002/adfm.201102191 Hong, 2009, Aggregation-induced emission: phenomenon, mechanism and applications, Chem Commun, 4332, 10.1039/b904665h Dong, 2007, Aggregation-induced emissions of tetraphenylethene derivatives and their utilities as chemical vapor sensors and in organic light-emitting diodes, Appl Phys Lett, 91, 10.1063/1.2753723 Liu, 2009, Aggregation-induced emission of silole molecules and polymers: fundamental and applications, J Inorg Organomet Polym, 19, 249, 10.1007/s10904-009-9282-8 Lei, 2015, Multi-stimulus-responsive fluorescent properties of donor-π-acceptor indene-1,3-dionemethylene-1,4-dihydropyridine derivatives, J Phys Chem C, 119, 23138, 10.1021/acs.jpcc.5b06432 Zheng, 2014, Piezofluorochromic properties of AIE-active 9,10-bis(N-alkylphenothiazin-3-yl-vinyl-2)anthracenes with different length of alkyl chains, Dyes Pigments, 102, 29, 10.1016/j.dyepig.2013.10.020 Alam, 2016, A multi-stimuli responsive “AIE” active salicylaldehyde-based Schiffbase for sensitive detection of fluoride, Sensor Actuator B Chem, 228, 539, 10.1016/j.snb.2016.01.024 Gopikrishna, 2018, Functional 1,8-naphthalimide AIE/AIEEgens: recent advances and prospects, ACS Appl Mater Interfaces, 10, 12081, 10.1021/acsami.7b14473 Londesborough, 2017, Thermochromic fluorescence from B18H20(NC5H5)2: an inorganic–organic composite luminescent compound with an unusual molecular geometry, Adv. Opt. Mater., 5, 1600694, 10.1002/adom.201600694 Xiong, 2015, Significant effect of alkyl chain length on fluorescent thermochromism of 9,10-bis(p-alkoxystyryl)anthracenes, RSC Adv, 5, 53255, 10.1039/C5RA08809G Chen, 2014, 1,8-Naphthalimide-based highly blue-emissive fluorophore induced by a bromine atom: reversible thermochromism and vapochromism characteristics, RSC Adv, 4, 63985, 10.1039/C4RA12091D Hariharan, 2015, Self-reversible mechanochromism and thermochromism of a triphenylamine-based molecule: tunable fluorescence and nanofabrication studies, J Phys Chem C, 119, 9460, 10.1021/acs.jpcc.5b00310 Wei, 2013, Reversible thermochromism of aggregation-induced emission-active benzophenone azine based on polymorph-dependent excited-state intramolecular proton transfer fluorescence, J Phys Chem C, 117, 3467, 10.1021/jp311020w Naito, 2017, Highly-efficient solid-state emissions of anthracene–o-carborane dyads with various substituents and their thermochromic luminescence properties, J Mater Chem C, 5, 10047, 10.1039/C7TC02682J Zhou, 2017, 5-(2,6-Bis((E)-4-(dimethylamino)styryl)-1-ethylpyridin-4(1H)-ylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione: aggregation-induced emission, polymorphism, mechanochromism, and thermochromism, J Mater Chem C, 5, 9264, 10.1039/C7TC02746J Ohtani, 2017, A flexible, fused, azomethine–boron complex: thermochromic luminescence and thermosalient behavior in structural transitions between crystalline polymorphs, Chem Eur J, 23, 11827, 10.1002/chem.201702309 Ma, 2016, Cyano-functionalized 1,4-bis((E)-2-(1H-indol-3-yl)vinyl)benzenes with aggregation induced emission characteristic and diverse thermochromic behaviour, Dyes Pigments, 126, 194, 10.1016/j.dyepig.2015.12.002 Taniguchi, 2014, Stimuli-responsive fluorescence of AIE elastomer based on PDMS and tetraphenylethene, Macromolecules, 47, 6382, 10.1021/ma501198d Löwe, 2002, Oligo(p‐phenylene vinylene) excimers as molecular probes: deformation‐induced color changes in photoluminescent polymer blends, Adv Mater, 14, 1625, 10.1002/1521-4095(20021118)14:22<1625::AID-ADMA1625>3.0.CO;2-Q Crenshaw, 2005, Phase separation of excimer‐forming fluorescent dyes and amorphous polymers: a versatile mechanism for sensor applications, Adv Mater, 17, 1471, 10.1002/adma.200401688 Kinami, 2006, Polyesters with built-in threshold temperature and deformation sensors, Chem Mater, 18, 946, 10.1021/cm052186c Crenshaw, 2006, Self-assessing photoluminescent polyurethanes, Macromolecules, 39, 9581, 10.1021/ma061685b Kunzelman, 2006, Self-assembly and dispersion of chromogenic molecules: a versatile and general approach for self-assessing polymers, Macromol Rapid Commun, 27, 1981, 10.1002/marc.200600642 Sing, 2009, Time–temperature indicators for high temperature applications, J Mater Chem, 19, 104, 10.1039/B813644K Crenshaw, 2007, Threshold temperature sensors with tunable properties, Macromol Chem Phys, 208, 572, 10.1002/macp.200600622 Kunzelman, 2008, Shape memory polymers with built-in threshold temperature sensors, J Mater Chem, 18, 1082, 10.1039/b718445j Pucci, 2007, Bis(benzoxazolyl)stilbene excimers as temperature and deformation sensors for biodegradable poly(1,4-butylene succinate) films, J Mater Chem, 17, 783, 10.1039/B612033D Donati, 2009, New cyclic olefin copolymer for the preparation of thermally responsive luminescent films, Macromol Chem Phys, 210, 728, 10.1002/macp.200800607 Pucci, 2010, Threshold temperature luminescent indicators from biodegradable poly(lactic acid)/poly(butylene succinate) blends, J Mater Chem, 20, 5843, 10.1039/c0jm00057d Pucci, 2011, Polymer composites with smart optical properties, Soft Matter, 7, 3689, 10.1039/c0sm01038c Bao, 2013, Reversible thermochromic switching of fluorescent poly(vinylidene fluoride) composite containing bis(benzoxazolyl)stilbene dye, Dyes Pigments, 99, 99, 10.1016/j.dyepig.2013.04.005 Bao, 2013, Reversible mechanochromism of a luminescent elastomer, ACS Appl Mater Interfaces, 5, 4625, 10.1021/am4013648 Itami, 2005, Triarylethene-based extended ð-systems: programmable synthesis and photophysical properties, J Org Chem, 70, 2778, 10.1021/jo0477401 An, 2010, Synthesis of 1,4-Bis[2,2-bis(4-alkoxyphenyl)vinyl]benzenes and Side Chain Modulation of Their Solid-State Emission, Org Lett, 12, 4364, 10.1021/ol101847w Jones, 1985, Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism, J Phys Chem, 89, 294, 10.1021/j100248a024 Zhang, 2014, Solvatochromic AIE luminogens as supersensitive water detectors in organic solvents and highly efficient cyanide chemosensors in water, Chem Sci, 5, 2710, 10.1039/c4sc00721b Gaussian 09, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr, J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, 2013. Phukan, 2015, Intramolecular charge transfer in coumarin based donor-acceptor systems: formation of a new product through planar intermediate, J Photochem Photobiol A, 303–304, 67, 10.1016/j.jphotochem.2015.02.007 Freidzon, 2012, Solvatofluorochromism and twisted intramolecular charge-transfer state of the nile red dye, Int J Quant Chem, 112, 3059, 10.1002/qua.24233 Kulinich, 2016, Scope of negative solvatochromism and solvatofluorochromism of merocyanines, Phys Chem Chem Phys, 18, 3444, 10.1039/C5CP06653K