SUCCESS2016-08-04T23:17:41.043940c21790d4-1bb1-4110-9b91-fffd2b809738C1(=CC=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=CC=C1compounds1nstoluene6.97tolueneΦf1.09,10-diphenylanthraceneDPAtoluene× 10 − 41.21toluene× 10 − 41.25toluene× 10 − 40.76CC=1C2=CC=CC=C2C(=C2C=CC=CC12)C29,10-dimethylanthracenetolueneΦf∼0.7toluene× 10 − 40.92toluene× 10 − 40.955toluene× 10 − 40.56C1(=CC=CC=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=NC=C1KBrcm−13429bscm−1m3061cm−1m2922cm−1m2851cm−1w2359cm−1w1941cm−1w1809cm−1w1704cm−1w1646cm−1s1592cm−1m1538cm−1w1519cm−1m1495cm−1s1438cm−1s1390cm−1m1324cm−1m1254cm−1m1212cm−1m1167cm−1m1145cm−1m1118cm−1m1068cm−1s1025cm−1m989cm−1m945cm−1w915cm−1w901cm−1w877cm−1w849cm−1m817cm−1s768cm−1s703cm−1m673cm−1s651cm−1s610cm−1s527cm−1w427CDCl38.88Hzdd2H4.37.74–7.702Hm7.64–7.555Hm7.49–7.464Hm7.40–7.334Hm400 MHz Varian NMR400H1MHzCDCl3150.05147.74138.66138.21131.16129.76129.06128.46127.64127.21126.58126.00125.68125.1400 MHz Varian NMR400C13MHzderivativescompoundsproduct3°C280.7tolueneΦf0.96±0.020nstoluene6.934-(10-phenylanthracene-9-yl)pyridinetoluene× 10 − 41.21toluene× 10 − 41.28toluene× 10 − 40.79C1(=CC=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=C(C=C1)C(F)(F)Fneatcm−13061bwcm−1w2820cm−1m1615cm−1w1494cm−1m1440cm−1m1402cm−1m1393cm−1s1324cm−1s1161cm−1s1117cm−1m1020cm−1m942cm−1m835cm−1s770cm−1s760cm−1m700cm−1s666cm−1m624cm−1s610cm−1m515cm−1m440cm−1m421CDCl3−62.38400 MHz Varian NMR400F19MHzCDCl37.88Hzd2H8.087.72–7.702Hm7.64–7.566Hm7.49–7.472Hm7.38–7.334Hm400 MHz Varian NMR400H1MHzCDCl3143.15138.78137.87135.16131.76131.20129.98129.80129.66129.60128.44127.58127.13126.32125.46125.41125.11400 MHz Varian NMR400C13MHzproductderivativescompounds4°C254.7tolueneΦf1.0±0.010nstoluene6.849-phenyl-10-(4-(trifluoromethyl)phenyl)anthracenetoluene× 10 − 41.22toluene× 10 − 41.29toluene× 10 − 40.795C1(=CC=CC=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C1=CC=C(C#N)C=C1neatcm−13056bwcm−1m2230cm−11934bwcm−1w1815cm−1m1603cm−1m1497cm−1m1438cm−1m1390cm−1w1271cm−1w1253cm−1w1190cm−1w1106cm−1w1069cm−1m1027cm−1m941cm−1w896cm−1w880cm−1m849cm−1m834cm−1w793cm−1s764cm−1w734cm−1s700cm−1s669cm−1m641cm−1s611cm−1s555cm−1w521cm−1w501cm−1m421CDCl37.94–7.91Hzdt2H8.47.73–7.692Hm7.63–7.612Hm7.60–7.524Hm7.48–7.462Hm7.39–7.334Hm400 MHz Varian NMR400H1MHzCDCl3144.53138.63138.26134.47132.29131.15129.77129.36128.46127.65127.24125.98125.69125.17118.90111.6031.37400 MHz Varian NMR400C13MHzproductcompounds5°C281.6tolueneΦf0.99±0.003nstoluene5.544-(10-phenylanthracene-9-yl)benzonitriletoluene× 10 − 41.24toluene× 10 − 41.31toluene× 10 − 40.80COC1=CC=C(C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=CC=C1neatcm−1w3068cm−1w3041cm−1m2997cm−1m2961cm−1w2839cm−11955bwcm−11888bwcm−1w1815cm−1w1708cm−1w1636cm−1m1607cm−1m1573cm−1s1512cm−1m1496cm−1m1461cm−1m1439cm−1w1408cm−1m1390cm−1w1369cm−1w1303cm−1m1284cm−1s1241cm−1m1181cm−1m1104cm−1m1070cm−1s1027cm−1m941cm−1w915cm−1w877cm−1m848cm−1s830cm−1w791cm−1s770cm−1s755cm−1w731cm−1w714cm−1s704cm−1s665cm−1m638cm−1m627cm−1s611cm−1m578cm−1m534cm−1w498cm−1m418CDCl37.77–7.732Hm7.70–7.672Hm7.63–7.523Hm7.49–7.472Hm7.42–7.382Hm7.36–7.302Hm7.17–7.132Hm3.973Hs400 MHz Varian NMR400H1MHzCDCl3218.85159.00139.11136.91136.89132.36131.31131.08130.19129.89128.37127.41127.02126.93124.93124.8855.38400 MHz Varian NMR400C13MHzproductcompounds6°C233.6tolueneΦf0.84±0.065nstoluene5.509-(4-methoxyphenyl)-10-phenylanthracenetoluene× 10 − 41.245toluene× 10 − 41.32toluene× 10 − 40.815C1(=CC=CC=C1)C1=C2C=CC=CC2=C(C2=CC=CC=C12)C=1SC=CC1KBrcm−13060bmcm−1w1947cm−1w1806cm−1w1708cm−1w1598cm−1w1518cm−1m1438cm−1m1377cm−1m1389cm−1w1286cm−1m1222cm−1w1161cm−1w1112cm−1w1070cm−1m1027cm−1m931cm−1m834cm−1s765cm−1m741cm−1m702cm−1s692cm−1m670cm−1s651cm−1w632cm−1s611cm−1w596cm−1w487cm−1m511cm−1w487cm−1w446cm−1m416CDCl37.90–7.882Hm7.69–7.672Hm7.63Hzdd1H1.27.61–7.58400 MHz Varian NMR400H1MHzCDCl3139.23138.82138.50131.55131.16129.78129.46128.73128.40127.55127.16126.94126.68126.66125.51125.11400 MHz Varian NMR400C13MHzproduct7°C197.0tolueneΦf0.09±0.0022-(10-phenylanthracen-9-yl)thiophenetoluene× 10 − 41.255toluene× 10 − 41.315toluene× 10 − 40.8S1C(=CC=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C=1SC=CC1KBrcm−1w3102cm−1w3058cm−1m2921cm−1m2851cm−1w1789cm−1w1717cm−1w1529cm−1w1448cm−1m1435cm−1m1372cm−1m1328cm−1w1258cm−1m1221cm−1w1173cm−1w1146cm−1w1136cm−1m1101cm−1m1036cm−1m1025cm−1w957cm−1m904cm−1m848cm−1s817cm−1s767cm−1m741cm−1s692cm−1s670cm−1m652cm−1m643cm−1m612cm−1m602cm−1m510cm−1w490cm−1m415CDCl37.89–7.854Hm7.63Hzdd2H1.27.43–7.394Hm7.32Hzdd2H3.47.22Hzdd2H1.2400 MHz Varian NMR400H1MHzCDCl3138.88131.42130.21129.51127.17126.79126.65125.6477.3277.0076.68400 MHz Varian NMR400C13MHzproduct8°C246.1tolueneΦf0.02±0.0009,10-di(thiophene-2-yl)anthracenetoluene× 10 − 41.35toluene× 10 − 41.365toluene× 10 − 40.815KBrcm−13068bwcm−1w2878cm−1w1929cm−11805bwcm−11712bwcm−1m1614cm−1w1574cm−1w1519cm−1m1439cm−1m1404cm−1m1380cm−1s1319cm−1m1222cm−1m1185cm−1s1160cm−1s1141cm−1s1113cm−1s1104cm−1s1065cm−1m1020cm−1w956cm−1m932cm−1w860cm−1w850cm−1m836cm−1s825cm−1s764cm−1m748cm−1m741cm−1w708cm−1s692cm−1m674cm−1s659cm−1m634cm−1s615cm−1m596cm−1m511cm−1w494cm−1w464cm−1m442cm−1m417CDCl37.904Hm7.65Hzdd1H1.27.62–7.564Hm7.44–7.335Hm7.24Hzdd1H1.2400 MHz Varian NMR400H1MHzCDCl3142.89138.86136.53131.62131.48130.10129.77129.58129.53127.20126.85126.82126.31125.64125.60125.47125.43109.99400 MHz Varian NMR400C13MHzCDCl3−62.39400 MHz Varian NMR400F19MHzproduct9°C261.4tolueneΦf0.026±0.006toluene× 10 − 41.28toluene× 10 − 41.32toluene× 10 − 40.80(2-(10-(4-trifluoromethyl)phenyl)anthracen-9-yl)thiopheneCOC1=CC=C(C=C1)C=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=C(C=C1)C(F)(F)FKBrcm−13065bwcm−1w2953cm−11939bwcm−11817bwcm−1m1613cm−1m1605cm−1w1574cm−1m1510cm−1m1460cm−1m1440cm−1m1403cm−1m1392cm−1w1367cm−1s1321cm−1m1286cm−1m1242cm−1m1175cm−1s1158cm−1s1120cm−1s1104cm−1s1065cm−1m1036cm−1m1021cm−1m942cm−1w883cm−1w866cm−1m848cm−1s826cm−1m818cm−1w708cm−1s771cm−1s751cm−1w730cm−1s672cm−1w644cm−1m633cm−1w621cm−1m610cm−1w591cm−1m577cm−1m533cm−1w506cm−1m430cm−1m421CDCl3159.10137.69134.99132.28131.76130.78130.14129.63127.22126.31125.43125.40125.02113.9055.39400 MHz Varian NMR400C13MHzCDCl3−62.36400 MHz Varian NMR400F19MHzCDCl37.88Hzd2H7.97.79–7.752Hm7.62Hzd2H7.87.60–7.562Hm7.41–7.336Hm7.15Hzdt2H8.73.973Hs400 MHz Varian NMR400H1MHzproductcompounds10°C305.7tolueneΦf0.77±0.016nstoluene4.699-(4-methoxyphenyl)-10-(4-(trifluoromethyl)phenyl)anthracenetoluene× 10 − 41.23toluene× 10 − 41.30toluene× 10 − 40.80BrC1=C2C=CC=CC2=C(C2=CC=CC=C12)C=1SC=CC1112-(10-bromoanthracene-9-yl)thiopheneproductCDCl38.59Hzd2H8.97.83Hzd2H8.97.63–7.581Hm7.46–7.421Hm7.32–7.281Hm7.20–7.171Hm400 MHz Varian NMR400H1MHzBrC=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=C(C=C1)OC129-bromo-10-(4-methoxyphenyl)anthraceneproductCDCl38.60Hzd2H9.57.70Hzd2H8.27.60–7.562Hm7.39–7.362Hm7.31Hzd2H7.57.12Hzd2H7.63.953Hs400 MHz Varian NMR400H1MHzC(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC.[Zn]zinc octaethyl porphyrinzinc octaethylporphyrinC1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)Ctri-o-tolylphosphinetri-o-tolyl phosphineBrC=1C2=CC=CC=C2C(=C2C=CC=CC12)C1=CC=CC=C19-bromo-10-phenylanthracene9-Bromo-10-phenylanthraceneC1(=CC=CC=C1)*phenylPhenylC(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC.[Pd]palladium octaethylporphyrinPdOEPC1=CC=CC2=CC3=CC=CC=C3C=C12anthraceneAnthraceneC(C)C1=C(C=2C=C3C(=C(C(=CC=4C(=C(C(=CC5=C(C(=C(N5)C=C1N2)CC)CC)N4)CC)CC)N3)CC)CC)CC.[Pt]PtOEPplatinum octaethylporphyrinaromatic phenylmetalloporphyrins[Pd]PdPt octaethylporphyrin[Pt]platinumquartz-halogenO=[Si]=Oquartzthiophene-substitutentsarylboronic acid2-Bu3Sn-thiophenePd2(dba)3CF3-Ph-B(OR)24-pyridine boronic acid pinacole ester[Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCCAliquat 336COMeOHC25H17N1538 ( m ) 1519 ( w ) 1495 ( m ) 1438 ( s ) 1390 ( s ) 1324 ( m ), 1254 ( m ) 1212FC(C1=CC=C(C=C1)B(O)O)(F)F4-(trifluoromethyl)phenyl boronic acidC27H17F3C(#N)C1=CC=C(C=C1)B(O)O4-cyanophenyl boronic acidC(C)OethanolC27H17NC27H20OC24H16SC22H14S2C25H15F3SC27H19F3OC1=CC=CC2=CC3=CC=CC=C3C=C12.S1C=CC=C1thiophene–anthraceneNa2CO3(aq)K2CO3(aq)phenyl-substituted anthracenes 3–6thiophenesS1C=CC=C1.C1=CC=CC2=CC3=CC=CC=C3C=C12anthracene–thiopheneanthracene–phenylc1ccc(cc1)c2ccccc2diphenyltrifluoro-substitutedS2–S11aryl9,10-disubstituted anthracenediphenylanthracenes[H]*hydrogenhydrogens1,4,5,8-anthraceneCC(C)=CCO[P](O)(=O)O[P](O)(O)=ODMAphenyl-substituted 9,10-anthracenes9,10-substituted anthraceneC3SESS[O]oxygenK2CO3NC1=NC(=O)N(C=C1)[C@H]2C[C@H](O)[C@@H](CO[P](O)(O)=O)O2DCMCOC1=CC=C(C=C1)B(O)O4-methoxyphenyl boronic acidNc1ncnc2n(cnc12)[C@@H]3O[C@H](CO[P](O)(=O)O[P](O)(O)=O)[C@@H](O)[C@H]3O[P](O)(O)=OATR4-(trifluoro)phenyl boronic acidC(C)(C)(C)[SnH2]C=1SC=CC12-(tertbutylstannyl)-thiophene1HC1(=CC=CC=C1)C=1C2=CC=CC=C2C=C2C=CC=CC129-phenylanthracenephenyl-substituentsO=[Si]=OsilicaBrC=1C2=CC=CC=C2C(=C2C=CC=CC12)Br9,10-dibromoanthracene[N]nitrogen[Na+].[Na+].[O-]C([O-])=ONa2CO3[H]H2HS1C=CC=C1thiopheneN#NN2Pd(PPh3)4[Na+].[Na+].[O-][S]([O-])(=O)=ONa2SO4CCCCCChexaneC1CCOC1THFanthracenesC1(=CC=CC=C1)CtolueneCDCl3TTA-UCtripletannihilationupconversionDPA9,10-diphenylanthraceneCMOLEDsorganiclightemittingdiodesTTAtripletannihilationISCintersystemcrossingTETtriplet-energytransferTTAtripletannihilationISCintersystemcrossingTETtripletenergytransferPtOEPplatinumoctaethylporphyrinCMTCSPCtimecorrelatedsinglephotoncountingPtOEPplatinumoctaethylporphyrinCMPdOEPpalladiumoctaethylporphyrinCMΔεSTΔεET),thesensitizertripletabsorptivityaphosastwoscalingfactorsfortherelativemagnitudeofphosphorescenceSNICSwedishNationalInfrastructureforComputingESIElectronicsupplementaryinformationRoyal Society of Chemistry10.1039/c5tc02626aenhttp://creativecommons.org/licenses/by/3.0/Journal of Materials Chemistry Chttp://pubs.rsc.org/en/Content/ArticlePDF/2015/TC/C5TC02626Ahttp://pubs.rsc.org/en/Content/ArticleLanding/2015/TC/C5TC02626Ahttp://pubs.rsc.org/en/Content/ArticleHTML/2015/TC/C5TC02626A11111c21790d4-1bb1-4110-9b91-fffd2b809738.html311121Victor GrayDamir DzeboAngelica LundinJonathan AlborzpourMaria AbrahamssonBo AlbinssonKasper Moth-PoulsenVictor GrayDamir DzeboAngelica LundinJonathan AlborzpourMaria AbrahamssonBo AlbinssonKasper Moth-Poulsen2015-10-22T00:00:00422015-09-21T00:00:00