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