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Introduc)onFluorescentpolycycliccompoundshavemanyfuturetechnologicalapplica6onsincluding:§ Biologicalassays,suchasimmunoassays
§ Allowingthemonitoringofcellhealth,growth,andenzyma6cac6vi6es,etc.
§ OrganicLightEmiAngDiodes(OLEDs)§ Showingthepoten6altobeaenergy-efficientlight
source§ OrganicField-EffectTransistors(OFETs)
§ Useasanorganicsemiconductor§ Solid-stateligh6ngandlasers
TargetCompounds
§ Synthesisofnovelmolecularstructureswithexpectedstrong
fluorescentproper6es§ Onepotsynthesisfromcommerciallyavailablematerials
SynthesisandCharacteriza)onofNovelFluorescentBoronContainingMolecules
NicolleS.Jackson,AndrewSchroder,SarahHarrell,JamieA.Trindell,SeJungGregory,AlexT.VegaDr.MichaelT.Huggins,Dr.AlanSchrock,Dr.PamelaP.Vaughan,Dr.KarenMolek,Dr.CarlSaint-Louis
DepartmentofChemistry,UniversityofWestFlorida,Pensacola,Florida32514
Calcula)ngQuantumYieldsACary-EclipseFluorescenceSpectrophotometerwasusedtoevaluatethefluorescenceefficiencyorquantumyield(Ф)versusaknownfluorescencestandard.1§ Inordertoensuretheinstrumentswereinproperworkingorder,
twostandards,DPAandanthracene,werecross-calibratedwitheachother.
AistheabsorpAonattheexcitaAonwavelength;Fistheintegratedemissionarea;ηistherefracAveindexofthesolventused;forsample(s)andreference(r)respecAvely.
Conclusion§ Sevennovelmoleculesweresuccessfullysynthesized.These
reac6onswereexecutedinaone-potreac6ons.§ Furthercharacteriza6oniscurrentlyunderway.§ Thesefluorescentmoleculesassistinprovidingfurther
understandingoftheproper6esoffluorescenceandtunableemission.
N-ConfusedFluorescentDipyrrinones
Non-DipyrrinoneAnalogs
References:1)Brower,A.M.StandardsforPhotoluminesceneQuantumYieldMeasurementsinSoluAon.PureAppl.Chem.2011,83(12);2213-2228.2)Boiadjiev,S.E.;Lightner,D.A.ReadilySynthesizedNovelFluorescentDipyrrinones.J.Org.Chem.2005,70,688-691.
SynthesisofTargetCompounds
FutureDirec)ons§ Possibleincorpora6onintopolymersforuseinOLEDtechnology§ Synthesisofaddi6onalnovelmoleculeswithdifferingintensityof
fluorescence,showingawidervarietyincolorsproduceduponexcita6on
§ Addi6onalmethodsofcharacteriza6onincludinghighresolu6on-massspectrometry(HRMS)
§ GrowthofsuitablecrystalsforX-raycrystallography
X-rayCrystalStructures
SuitablecrystalsgrownfromslowdiffusionofhexaneintoaCH2Cl2solu6onofthetargetcompound
X-RayCrystalStructureofCompound4
X-RayCrystalStructureofCompound5
4
Op)calProper)es
TableofFluorescenceData
TableofUV-VisibleDataCompound CHCl3
lmax*(ε)CH3OHlmax*(ε)
DMSOlmax*(ε)
CH3CNlmax*(ε)
C6H14lmax*(ε)
DMSO/H2Olmax*(ε)
2 396(40000)
396.2(11100)
420.3(12200)
392.3(10700)
NotSoluble
399.7(7500)
3 370.8(17300)
370.3(11800)
372.8(15100)
369.2(12900)
365.8(13300) NotSoluble
4 433.7(12200)
433.2(13000)
433.5(16800)
433.3(15000)
428.7(16500)
436.5(14500)
5 362.3(19700)
360.1(25800)
359(16000)
358.5(17700)
377.7(37600)
358.9(26700)
6 388.7(49600)
395.8(9640)
396.8(8260)
384.6(12400)
381.7(15100)
396.9(6880)
*λmaxinnm;εinM-1cm-1
Compound CHCl3λem*(φF)
CH3OHλem*(φF)
DMSOλem*(φF)
CH3CNλem*(φF)
C6H14λem*(φF)
DMSO/H2Oλem*(φF)
2 468.0(0.31)
501.0(0.513)
482.9(0.50)
470.9(0.32)
N/A**(N/A**)
508.8(0.39)
3 401.4(N/A**)
508.3(N/A**)
408.0(N/A**)
426.8(N/A**)
419.8(N/A**)
N/A**(N/A**)
4 468.9(0.59)
510.0(0.436)
485.0(0.589)
476.1(0.536)
458.9(0.261)
520.0(0.31)
5 418.0(0.36)
410.9(0.117)
415.8(0.19)
410.9(0.42)
404.9(0.25)
429.8(0.114)
6 476.1 517.9 461.06 491.1 440.9 530.0
*λeminnm;**belowdetectablelimits
Compound1 Compound2 Compound3 Compound4 Compound5 Compound6 Compound7
NMRCharacteriza)on
1.52.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm
1.130
1.149
1.168
1.571
2.178
2.405
2.423
2.442
2.461
3.926
6.681
6.861
7.260
7.502
3.00
2.96
1.99
6.07
0.99
0.97
0.98
1.52.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm
1.123
1.141
1.160
1.537
2.150
2.400
2.420
2.438
2.457
6.452
6.459
6.495
6.504
6.511
7.259
7.721
7.726
3.00
3.64
1.99
2.77
0.85
1.52.02.53.03.54.04.55.05.56.06.57.07.5 ppm
1.120
1.139
1.158
1.546
2.140
2.362
2.381
2.400
2.419
6.027
6.296
6.876
7.258
7.476
7.510
3.13
3.02
2.00
2.01
0.98
0.97
1.75
1.52.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm
1.118
1.137
1.156
1.387
1.405
1.423
1.537
2.123
2.394
2.413
2.432
2.451
2.741
4.360
4.377
4.395
4.412
6.335
7.259
2.50
2.95
2.84
1.87
2.86
1.98
1.00
1.52.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm
1.124
1.143
1.162
1.550
2.150
2.371
2.390
2.409
2.428
6.484
7.259
7.382
7.387
7.934
8.077
3.11
3.00
2.09
0.91
0.93
0.83
0.87
Compound2
Compound3
Compound4
Compound5
Compound6
Compound1
Compound7
1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0 ppm
1.136
1.155
1.174
2.385
2.404
2.423
2.442
6.430
7.356
7.374
7.392
7.427
7.446
7.516
7.534
7.553
7.648
8.085
8.104
3.05
3.03
2.03
1.00
0.99
1.01
1.02
0.90
0.97
1.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5 ppm
1.142
1.161
1.180
2.195
2.430
2.449
2.467
2.486
6.534
7.479
7.490
7.497
7.619
7.638
7.654
8.437
8.458
3.04
3.03
2.26
1.09
2.01
1.00
0.95