, HRMS (ESI + ) calcd for C30H23N4O [M+H] + : 455.1866, found: 455.1857; UV-Vis (CH2Cl2) ?max = 565 nm (? = 42 000 L.mol -1 .cm -1 ). 2.2.12 3-cyano-4-[2-[4-(diphenylamino)phenyl]ethenyl, pp.5-7, 1168.
, mL) and toluene (0.5 mL) using general protocol 2 Purification by chromatography (EtOAc/Petroleum ether: 30/70) afforded the title compound 1g Red solid (340 mg, yield = 83%); m.p. 171°C; 1 H-NMR (CD2Cl2, 500 MHz, From 1 (273 mg, 1 mmol) and G (151 mg, 1 mmol) in acetonitrile), 7.17 (t, J = 7.8 Hz, 6H), 6.99 Hz, 1H), 1.65 (s, 6H); 13 C-NMR (CD2Cl2, 125 MHz x CH), pp.167-169
x CH 3 ); IR (?/cm -1 ) 2223 (?CN), 1735 (?CO) HRMS (ESI + ) calcd for C27H22N2O2Na [M+Na] + : 429.7573, found: 429.1570; UV-Vis (CH2Cl2) ?max = 484 nm (? = 38 400 L.mol -1 .cm -1 ). 2.2.13 3-methyl ester-4-[2-[4-(diphenylamino)phenyl]ethenyl, mmol.) following general protocol 1 (80°C, 24 h), pp.5-7, 1175. ,
80) afforded the title compound 1h Yellow solid (350 mg, yield = 74%); m.p. 174 °C; 1 H-NMR (CDCl3, 500 MHz, pp.36-43 ,
x CH 3 ); IR (?/cm -1 ) 1736 (?CO) HRMS (ESI + ) calcd for C28H25NO4Na [M+Na] + : 462.1676, found: 462.1656; UV-Vis (CH2Cl2) ?max = 483 nm (? = 31 300 L.mol -1 .cm -1 ). 2.2.14 3-(2-benzothiazolyl)-4-[2-[4-(diphenylamino)phenyl]ethenyl]-5,5-dimethyl-2- butenolide (1i) From 1 (273 mg, 1 mmol.) and I (259 mg, 1 mmol.) in acetonitrile (3 mL) and toluene (0.5 mL) according to general protocol 2. The microwave irradiations were applied at 100°C for 3 h. Purification by chromatography (EtOAc/Cyclohexane: 30/70) afforded the title compound 1i, C-NMR (CDCl2, 125 MHz 80%); m.p. 165-170°C; 1 H-NMR (CD2Cl2, 500 MHz, ?/ppm) 8.83 (d, J = 17.0 Hz, 1H) 1H), 7.43 (dd, J = 7.5 Hz, 1H) x CH) x CH) x CH) x CH)CH)CH) x CH)CH), pp.887135-887142, 1050. ,
, HRMS (ESI + ) calcd for C33H27N2O2S [M+H] + : 515.1788, found: 515.1776; UV-Vis (CH2Cl2) ?max = 455 nm (? = 34 900 L.mol -1 .cm -1 ). 2.2.15 2-((9-ethyl-9H-carbazol-3-yl)methylene)-1H-indene-1, pp.3-5, 1024.
, 1.2 mmol.), following general protocol 1 (45°C, 26 h) Purification by chromatography (petroleum ether/EtOAc: 3/1 v/v) afforded the title compound 2a Orange solid (330 mg, yield = 78%); m.p. 230°C; 1 H-NMR (CD 2 Cl 2 , 500 MHz, mg, 1.5 mmol.) and A (175 mgppm) 9.46 (s, 1H), 8.72 (d, J = 8.7 Hz, 1H), 8.24 (d, J = 7.7 Hz, 1H), 8.08 (s, 1H), 8.01 (dd, J = 5.4, 2.7 Hz, 1H), 7.96 (dd, J = 5.2, 2.9 Hz, 1H)
, 35 (t, J = 7.4 Hz, 1H), 4.43 (q, J = 7.3 Hz, 2H), pp.7-7560
, C-NMR (CD2Cl2, 125 MHz 133.7 (CH), 129.0 (CH), 127.3 (CH) 110.0 (CH) HRMS (ESI + ) calcd for C24H18NO2 [M+H] + : 352.1332 Organic optoelectronics: Materials and devices for photonic applications, pp.1665-1571, 1129.
Progress and perspective of polymer white light-emitting devices and materials [3] Reisch A, Klymchenko AS. Fluorescent polymer nanoparticles based on dyes: Seeking brighter tools for bioimaging, Chem Soc Rev Small, vol.3812, issue.1215, pp.3391-4001968, 2009. ,
Fluorescent organic nanocrystals and non-doped nanoparticles for biological applications, Nanoscale, vol.5, issue.18, pp.8428-8470, 2013. ,
DOI : 10.1021/nn2013904
Aggregation-Induced Emission: Together We Shine, United We Soar!, Chemical Reviews, vol.115, issue.21, pp.11718-940, 2015. ,
DOI : 10.1021/acs.chemrev.5b00263
Aggregation-induced emission dyes for in vivo functional bioimaging ,
, Aggregation-induced emission: Fundamentals and applications, volumes 1 and 2: John Wiley and Sons Ltd, pp.209-246, 2013.
In vivo near-infrared fluorescence imaging, Current Opinion in Chemical Biology, vol.7, issue.5, pp.626-660, 2003. ,
DOI : 10.1016/j.cbpa.2003.08.007
Near-infrared fluorescence: application to in vivo molecular imaging, Current Opinion in Chemical Biology, vol.14, issue.1, pp.71-80, 2010. ,
DOI : 10.1016/j.cbpa.2009.09.029
Going deeper than microscopy: the optical imaging frontier in biology, Nature Methods, vol.11, issue.8, pp.603-617, 2010. ,
DOI : 10.1117/1.2400702
Aggregation-induced emission: The whole is more brilliant than the parts A tetraphenylethene-based red luminophor for an efficient non-doped electroluminescence device and cellular imaging, Current Protocols in Cytometry 2012:Unit12.27. [11], pp.5429-7911018, 2012. ,
Aggregation-induced red-NIR emission organic nanoparticles as effective and photostable fluorescent probes for bioimaging, Journal of Materials Chemistry, vol.5, issue.30, pp.15128-15163, 2012. ,
DOI : 10.1021/mp800049w
Organic dots with aggregation-induced emission (aie dots) characteristics for dual-color cell tracing Precise and long-term tracking of adiposederived stem cells and their regenerative capacity via superb bright and stable organic nanodots, Chem Mater ACS Nano, vol.258, issue.2112, pp.4181-712620, 2013. ,
Tetraphenylethene end-capped [1,2,5]thiadiazolo[3,4-c]pyridine with aggregation-induced emission and large two-photon absorption cross-sections, RSC Advances, vol.17, issue.2, pp.1500-1506, 2015. ,
DOI : 10.1002/chem.201002821
Fluorescence Bioimaging, Bioconjugate Chemistry, vol.22, issue.7, pp.1438-50, 2011. ,
DOI : 10.1021/bc2002506
Aggregation-induced emission of triphenylamine substituted cyanostyrene derivatives A new diketopyrrolopyrrole-based near-infrared (nir) fluorescent biosensor for bsa detection and aie-assisted bioimaging Biocompatible nanoparticles based on diketopyrrolo-pyrrole (dpp) with aggregation-induced red/nir emission for in vivo two-photon fluorescence imaging Polymorphism and luminescence properties of cmons organic crystals: Bulk crystals and nanocrystals confined in gel-glasses Second harmonic generation and fluorescence of cmons dye nanocrystals grown in a sol-gel thin film, Evolution of red organic light-emitting diodes: Materials and devices, pp.7013-201045, 2001. ,
Red-emitting fluorenes as efficient emitting hosts for non-doped, organic red-light-emitting diodes Multicolor emission of small molecule-based amorphous thin films and nanoparticles with a single excitation wavelength Molecular packing and solid-state fluorescence of alkoxy-cyano substituted diphenylbutadienes: Structure of the luminescent aggregates, K. Drastic solid-state fluorescence enhancement behaviour of phenanthro, pp.231-86597, 2005. ,
Unusual solid-state luminescent push?pull indolones: A general one-pot three-component approach Synthesis of carbazole-type d-?-a fluorescent dyes possessing solid-state red fluorescence properties Red emitting solid state fluorescent triphenylamine dyes: Synthesis, photo-physical property and dft study Substituent group variations directing the molecular packing, electronic structure, and aggregation-induced emission property of isophorone derivatives The combined effect of multiple forces, Eur J Org Chem Org Lett Eur J Org Chem Dyes Pigm J Org Chem J Org Chem, vol.1230201297327878, issue.3415253720, pp.5979-903364, 2009. ,
Systematic study and imaging application of aggregation-induced emission of ester-isophorone derivatives Five different colours solid-state fluorescence of azastilbenes: A new push?pull ?-conjugated system, the solid state High quantum yield both in solution and solid state based on cyclohexyl modified triphenylamine derivatives for picric acid detection, pp.4572-78531, 2014. ,
Aggregation induced emissive carbazole-based push pull nlophores: Synthesis, photophysical properties and dft studies Tuning solid-state fluorescence to the near-infrared: A combinatorial approach to discovering molecular nanoprobes for biomedical imaging, Dyes Pigm ACS Appl Mater Interfaces, vol.1245, issue.18, pp.82-928881, 2013. ,
Near-infrared solidstate emitters based on isophorone: Synthesis, crystal structure and spectroscopic properties Solid state red biphotonic excited emission from small dipolar fluorophores Unparalleled ease of access to a library of biheteroaryl fluorophores via oxidative cross-coupling reactions: Discovery of photostable nir probe for mitochondria Far-red and near-ir aie-active fluorescent organic nanoprobes with enhanced tumor-targeting efficacy: Shape-specific effects, Chem Mater J Mater Chem C J Am Chem Soc Angew Chem Int Ed, vol.23413854, issue.341425, pp.862-73766, 2011. ,
Structure and properties of a novel yellow emitting material for organic light-emitting diodes Isophorone-based analogues with a-?-d-?-a structure for red organic light emitting devices Red fluorescence thin film based on a strong push?pull dicyanoisophorone system A red to near-ir fluorogen: Aggregationinduced emission, large stokes shift, high solid efficiency and application in cell-imaging An easily accessible aggregation-induced emission probe for lipid droplet-specific imaging and movement tracking Aggregation induced two-photon absorption, Thin Solid Films Synth Met Dyes Pigm Chem Eur J Chem Commun RSC Adv, vol.51515946113472253496, issue.428565, pp.2403-95, 2006. ,
Study of red-emission piezochromic materials based on triphenylamine Second-order nonlinear optical compounds with good nonlinear optical properties and heat resistance. National Institute of Information and Communications Technology, Japan; Sumitomo Electric Industries D-?-a compounds with tunable intramolecular charge transfer achieved by incorporation of butenolide nitriles as acceptor moieties Formal aromatic c?h insertion for stereoselective isoquinolinone synthesis and studies on mechanistic insights into the c?c bond formation, ChemPlusChem Ltd J Org Chem J Org Chem Dyes Pigm, vol.81528074102, issue.72416, pp.637-682, 2009. ,
Synthesis, electronic, and electrooptical properties of emissive solvatochromic phenothiazinyl merocyanine dyes Synthesis and characterization of nonlinear optical chromophores containing -cyan with thermal stability, Chem Eur J Opt Mater, vol.172257, issue.361, pp.9984-9845, 2003. ,
, Synthesis and characterization of conjugated pyridine-(n-diphenylamino) acrylonitrile derivatives: Photophysical properties, J Mater Sci Res, vol.158, issue.2, pp.181-183, 2012.
Tricyanofuran-based donor?acceptor type chromophores for bulk heterojunction organic solar cells [60] Lakowicz JR. Appendix i. Corrected emission spectra Nonlinear optical active poly(adamantyl methacrylate-methyl vinyl urethane)s functionalised with phenyltetraene-bridged chromophore, Principles of fluorescence spectroscopy, pp.56271-56278, 2004. ,
Saturated and unsaturated lactones, J Chem Soc, Perkin Trans, vol.1, issue.11, pp.19991377-96 ,
Recent advances in annonaceous acetogenins Advances in the synthesis of natural butano-and butenolides Formation of five-and six-membered ,-unsaturated lactones through ring-closing metathesis of functionalized acrylates. Applications to synthesis of natural products The chemistry of -butenolides Unsaturated lactones. Ii. Synthesis of unsaturated -lactones by condensation of -ketoalcohols with acetoacetic and cyanoacetic esters Unsaturated lactones. I. Synthesis of substituted unsaturated -lactones by condensing tertiary -keto alcohols with malonic ester Synthesis of benzazoles with heterocyclic substituents and their condensation reactions with aldehydes, Recent advances in the chemistry of unsaturated lactones, pp.625-94275, 1970. ,
Synthesis of 2-(2,5-Dihydrofuran-3-yl)-2-oxoethyl carboxylates, Russian Journal of Organic Chemistry, vol.33, issue.6 ,
DOI : 10.1016/j.bmcl.2011.05.017
Cyclocondensation of 3-acetylfuran-2(5h)-ones with benzylidenemalononitrile. Synthesis of 3-(5-amino-4, pp.936-96, 2013. ,
Enhanced emission and its switching in fluorescent organic nanoparticles -conjugated cyanostilbene derivatives: A unique self-assembly motif for molecular nanostructures with enhanced emission and transport Towards highly luminescent phenylene vinylene films Tuning of fluorescence in films and nanoparticles of oligophenylenevinylenes, J Am Chem Soc Acc Chem Res Synth Met J Phys Chem B, vol.5112474457583102, issue.12484311, pp.1809-1214410, 1996. ,
Alkoxy-styryl dcdhf fluorophores A fluorescent polymer probe with high selectivity toward vascular endothelial cells for and beyond noninvasive twophoton intravital imaging of brain vasculature, PCCP ACS Appl Mater Interfaces, vol.12788, issue.2827, pp.7768-7117047, 2010. ,
Tight intermolecular packing through supramolecular interactions in crystals of cyano substituted oligo(para-phenylene vinylene): A key factor for aggregation-induced emission Organic nonlinear optical crystals based on configurationally locked polyene for melt growth, Chem Commun Chem Mater Acta Crystallogr Sect Sect E: Struct Rep Online, vol.188168, issue.31710, pp.231-34049, 2006. ,
Synthesis, crystal structures and nonlinear optical properties of three tcf-based chromophores 2-(p-diethylaminobenzylidene)-1,3-indandione J-aggregates: From serendipitous discovery to supramolecular engineering of functional dye materials, CrystEngComm Acta Crystallogr Sect C: Cryst Struct Commun Angew Chem Int Ed, vol.11528450, issue.41115, pp.589-962878, 1996. ,