Luminescent Donor-acceptor β-diketones: Modulation of emission by solvent polarity and group ii metal binding

Journal of Fluorescence

Volumn 19, Issue 5, 2009, Pages 881-889

  Zhang, Guoqing ^a   Kim, Shin Han ^b   Evans, Ruffin E ^a   Kim, Byeong Hyo ^b   Demas, J N ^a   Fraser, Cassandra L ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

^b Kwangwoon University   (South Korea)

Author keywords

Anthracene; Fluorescent diketones; Mg 2+ and Ca 2+ binding; Naphthalene; Solvatochromism

Indexed keywords

ASSOCIATION CONSTANT; BATHOCHROMIC SHIFT; BLUE SHIFT; DIFFERENT SOLVENTS; DIKETONES; DONOR-ACCEPTORS; EMISSION SPECTRUMS; ETHANOL SOLUTIONS; FLUORESCENCE QUANTUM YIELD; LIGHT EMITTING MATERIALS; METAL BINDING; MG 2+ AND CA 2+ BINDING; MOLECULAR PROBES; ONE STEP; ORDERS OF MAGNITUDE; SIMPLE STRUCTURES; SOLVATOCHROMISM; SOLVATOCHROMISMS; SOLVENT POLARITY; STRONG BINDING; TRIFLUOROMETHYL;

ANTHRACENE; BINDING ENERGY; CALCIUM; CHARGE TRANSFER; EMISSION SPECTROSCOPY; ETHANOL; FLUORESCENCE; INTERNET PROTOCOLS; ION EXCHANGE; LIGHT EMISSION; MAGNESIUM; NAPHTHALENE; SOLVENTS;

KETONES;

ACETIC ACID DERIVATIVE; ACETIC ACID ETHYL ESTER; ACETONITRILE DERIVATIVE; ALCOHOL; CALCIUM; DICHLOROMETHANE; FURAN DERIVATIVE; KETONE; MAGNESIUM; SOLVENT; TETRAHYDROFURAN; TOLUENE;

ARTICLE; CHEMISTRY; LUMINESCENCE; PHOTOCHEMISTRY; QUANTUM THEORY; SPECTROFLUOROMETRY; SYNTHESIS;

ACETATES; ACETONITRILES; CALCIUM; ETHANOL; FURANS; KETONES; LUMINESCENCE; MAGNESIUM; METHYLENE CHLORIDE; PHOTOCHEMISTRY; QUANTUM THEORY; SOLVENTS; SPECTROMETRY, FLUORESCENCE; TOLUENE;

EID: 70349322857     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-009-0487-6     Document Type: Article

References (40)

1. ZR Grabowski K Rotkiewicz W Rettig 2003 Structural changes accompanying intramolecular electron transfer: focus on twisted intramolecular charge-transfer states and structures Chem Rev 103 3899 4032 10.1021/cr940745l 14531716 10.1021/cr940745l
2. AP de Silva HQN Gunaratne T Gunnlaugsson AJM Huxley CP McCoy JT Rademacher TE Rice 1997 Signalling recognition events with fluorescent sensors and switches Chem Rev 97 1515 1566 10.1021/cr960386p 11851458 10.1021/cr960386p
3. G Yu J Gao JC Hummelen F Wudl AJ Heeger 1995 Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions Science 270 1789 1791 10.1126/science.270.5243.1789 10.1126/science.270.5243. 1789 1:CAS:528:DyaK2MXhtVSiurjF
4. P Peumans V Bulović SR Forrest 2000 Efficient high-bandwidth organic multilayer photodetectors Appl Phys Lett 76 3855 3857 10.1063/1.126800 10.1063/1.126800 1:CAS:528:DC%2BD3cXkt1Ggt7Y%3D
5. PE Burrows Z Shen V Bulović DM McCarty SR Forrest JA Cronin ME Thompson 1996 Relationship between electroluminescence and current transport in organic heterojunction light-emitting devices J Appl Phys 79 7991 8006 10.1063/1.362350 10.1063/1.362350 1:CAS:528:DyaK28XivFeqsrw%3D (Pubitemid 126626178)
6. F Meyers SR Marder BM Pierce JL Bredas 1994 Electric field modulated nonlinear optical properties of donor-acceptor polyenes: sum-over-states investigation of the relationship between molecular polarizabilities (alpha, beta, and gamma) and bond length alternation J Am Chem Soc 116 10703 10714 10.1021/ja00102a040 10.1021/ja00102a040 1:CAS:528:DyaK2cXms1Oiu7k%3D
7. Desvergne JP, Czarnik AW (1997) Chemosensors of ion and molecule recognition. Springer, London
8. S Fery-Forgues D Lavabre AD Rochal 1998 Strong interaction between a fluorescent β-diketone derivative and alkali and alkaline earth cations in solution studied by spectrophotometry N J Chem 22 1531 1538 10.1039/a802688b 10.1039/a802688b
9. C Pettinari F Marchetti A Drozdov 2003 β-Diketones and related ligands Coord Chem Rev II 1 97 115
10. E DeOliveira CR Neri OA Serra AGS Prado 2007 Antenna effect in highly luminescent Eu3+ anchored in hexagonal mesoporous silica Chem Mater 19 5437 5442 10.1021/cm701997y 10.1021/cm701997y 1:CAS:528:DC%2BD2sXhtFeisbrO (Pubitemid 350099814)
11. P Banet L Legagneux P Hesemann JJE Moreau L Nicole A Quach C Sanchez TH Tran-Thi 2008 Hybrid mesostructured thin films functionalized with DBM as new selective sensors of BF3 Sens Actuators B Chem 130 1 8 10.1016/j.snb.2007.07.103 10.1016/j.snb.2007.07.103
12. W Huang J Wang Q Shen X Zhou 2007 An efficient Yb(OTf) 3 catalyzed alkylation of 1, 3-dicarbonyl compounds using alcohols as substrates Tetrahedron Lett 48 3969 3973 10.1016/j.tetlet.2007.04.047 10.1016/j.tetlet.2007.04.047 1:CAS:528:DC%2BD2sXlt1Kjs74%3D (Pubitemid 46702265)
13. G Zhang J Chen SJ Payne SE Kooi JN Demas CL Fraser 2007 Multi-emissive difluoroboron dibenzoylmethane polylactide exhibiting intense fluorescence and oxygen-sensitive room-temperature phosphorescence J Am Chem Soc 129 8942 8943 10.1021/ja0720255 17608480 10.1021/ja0720255 1:CAS:528:DC%2BD2sXnt1Snsbo%3D (Pubitemid 47171825)
14. A Pfister G Zhang J Zareno AF Horwitz CL Fraser 2008 Boron polylactide nanoparticles exhibiting fluorescence and phosphorescence in aqueous medium ACS Nano 2 1252 1258 10.1021/nn7003525 19081748 10.1021/nn7003525 1:CAS:528:DC%2BD1cXmsFCrurg%3D
15. JL Gorczynski J Chen CL Fraser 2005 Iron tris(dibenzoylmethane)-centered polylactide stars: Multiple roles for the metal complex in lactide ring-opening polymerization J Am Chem Soc 127 14956 14957 10.1021/ja0530927 16248597 10.1021/ja0530927 1:CAS:528:DC%2BD2MXhtVKmtLjN (Pubitemid 41547325)
16. JL Bender PS Corbin CL Fraser DH Metcalf FS Richardson EL Thomas AM Urbas 2002 Site-isolated luminescent europium complexes with polyester macroligands: Metal-centered heteroarm stars and nanoscale assemblies with labile block junctions J Am Chem Soc 124 8526 8527 10.1021/ja0261269 12121083 10.1021/ja0261269 1:CAS:528:DC%2BD38XkslOisrk%3D (Pubitemid 34791012)
17. Cowan JA (1995) Biological chemistry of magnesium. VCH, New York
18. MJ Berridge MD Bootman HL Roderick 2003 Calcium signalling: dynamics, homeostasis and remodelling Nat Rev Mol Cell Biol 4 517 529 10.1038/nrm1155 12838335 10.1038/nrm1155 1:CAS:528:DC%2BD3sXltVWmsr8%3D (Pubitemid 36773404)
19. V Goldschmidt J Didierjean B Ehresmann C Ehresmann C Isel R Marquet 2006 Mg2+ dependency of HIV-1 reverse transcription, inhibition by nucleoside analogues and resistance Nucleic Acids Res 34 42 52 10.1093/nar/gkj411 16394022 10.1093/nar/gkj411 1:CAS:528:DC%2BD28Xmsl2ntg%3D%3D (Pubitemid 43160034)
20. T Kirschberg J Parrish 2007 Metal chelators as antiviral agents Curr Opin Drug Discov Devel 10 460 472 17659488 1:CAS:528:DC%2BD2sXosFCns7Y%3D
21. EJ Park M Brasuel C Behrend MA Philbert R Kopelman 2003 Ratiometric optical PEBBLE nanosensors for real-time magnesium ion concentrations inside viable cells Anal Chem 75 3784 3791 10.1021/ac0342323 14572044 10.1021/ac0342323 1:CAS:528:DC%2BD3sXkvVOrurs%3D (Pubitemid 36962112)
22. R Rudolf M Mongillo R Rizzuto T Pozzan 2003 Innovation: looking forward to seeing calcium Nat Rev Mol Cell Biol 4 579 586 10.1038/nrm1153 12838340 10.1038/nrm1153 1:CAS:528:DC%2BD3sXltVWnu7c%3D (Pubitemid 36773409)
23. M Uekawa Y Miyamoto H Ikeda K Kaifu T Nakaya 1997 Synthesis and luminescent properties of europium complexes Synth Met 91 259 262 10.1016/S0379-6779(97)04027-7 10.1016/S0379-6779(97)04027-7 1:CAS:528: DyaK1cXlslOntg%3D%3D
24. Y Li B Yan H Yang 2008 Construction, characterization, and photoluminescence of mesoporous hybrids containing europium(III) complexes covalently bonded to SBA-15 directly functionalized by modified β-diketone J Phys Chem C 112 3959 3968 10.1021/jp710023q 10.1021/jp710023q 1:CAS:528:DC%2BD1cXitVagu70%3D
25. λ1: anthracene moiety absorption maximum; λ2: charge-transfer band maximum
26. Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer, New York, p 54
27. Kawski A (1992) Progress in photochemistry and photophysics. In: Rabek F (ed). CRC, Boca Raton, pp. 1-47
28. ER Carraway JN Demas BA DeGraff 1991 Photophysics and photochemistry of oxygen sensors based on luminescent transition metal complexes Anal Chem 63 332 336 10.1021/ac00004a006 10.1021/ac00004a006 1:CAS:528:DyaK3MXlt1alsg%3D%3D
29. GA Crosby JN Demas 1971 The measurement of photoluminescence quantum yields J Phys Chem 75 991 1024 10.1021/j100678a001 10.1021/j100678a001 1:CAS:528:DyaE3MXktFamsL4%3D
30. C Bohne H Ihmels M Waidelich C Yihwa 2005 N-acylureido functionality as acceptor substituent in solvatochromic fluorescence probes: Detection of carboxylic acids, alcohols, and fluoride ions J Am Chem Soc 127 17158 17159 10.1021/ja052262c 16332043 10.1021/ja052262c 1:CAS:528:DC%2BD2MXht1SrsLrN (Pubitemid 41791015)
31. H Ihmels A Meiswinkel CJ Mohrschladt D Otto M Waidelich M Towler R White M Albrecht A Schnurpfeil 2005 Anthryl-substituted heterocycles as acid-sensitive fluorescence probes J Org Chem 70 3929 3938 10.1021/jo047841z 15876081 10.1021/jo047841z 1:CAS:528:DC%2BD2MXjtFehs74%3D (Pubitemid 40675323)
32. H Ihmels A Meiswinkel C Mohrschladt 2002 Novel fluorescence probes based on 2, 6-donor-acceptor-substituted anthracene derivatives J Org Lett 2 2865 2868 10.1021/ol006291y 10.1021/ol006291y
33. P Wang S Wu 1995 Spectroscopy and photophysics of bridged enone derivatives: effect of molecular structure and solvent J Photochem Photobiol Chem 86 109 113 10.1016/1010-6030(94)03921-G 10.1016/1010-6030(94)03921-G 1:CAS:528:DyaK2MXjs1Ggsr0%3D
34. E Iglesias 1996 Enolization of benzoylacetone in aqueous surfactant solutions: A novel method for determining enolization constants J Phys Chem 100 12592 12599 10.1021/jp960473l 10.1021/jp960473l 1:CAS:528:DyaK28XjvFCitr0%3D
35. E Iglesias 1997 Determination of keto-enol equilibrium constants and the kinetic study of the nitrosation reaction of β-dicarbonyl compounds J Chem Soc Perkin Trans 2 431 440 10.1039/a607039f
36. Y Sato M Morimoto H Segawa T Shimidzu 1995 Twisted intramolecular charge-transfer state of a donor-acceptor molecular system with a β-diketone bridge: tuning of emission through structural restriction by metal cation coordination J Phys Chem 99 35 39 10.1021/j100001a007 10.1021/j100001a007 1:CAS:528:DyaK2MXislejsrw%3D
37. LF Hatch G Sutherland 1948 Certain metal derivatives of 2, 4-pentanedione J Org Chem 13 249 253 10.1021/jo01160a012 18903741 10.1021/jo01160a012 1:CAS:528:DyaH1cXitlWnsw%3D%3D
38. JA Bertrand D Caine 1964 Preparation and properties of methoxo complexes of divalent metal ions J Am Chem Soc 86 2298 2299 10.1021/ja01065a048 10.1021/ja01065a048 1:CAS:528:DyaF2cXkt1aqu7k%3D
39. SW Thomas III K Venkatesan P Muller TM Swager 2006 Dark-field oxidative addition-based chemosensing : New bis-cyclometalated Pt(II) complexes and phosphorescent detection of cyanogen halides J Am Chem Soc 128 16641 16648 10.1021/ja065645z 17177413 10.1021/ja065645z 1:CAS:528:DC%2BD28XhtlSgsrbM (Pubitemid 46032743)
40. LG Van Ujtert 1983 Chelate compound stability constant calculations on metal diketonate complexes Polyhedron 2 285 269 10.1016/S0277-5387(00)83915-7 10.1016/S0277-5387(00)83915-7