Kinetic analysis of tautomer forms of aromatic-urea compounds with acetate ions: solvent effect of excited state intermolecular proton transfer.

In this paper, we report the solvent effect of excited state intermolecular proton transfer (ESIPT) reactions of urea compounds in the presence of tetrabutylammonium acetate (TBAAc). We prepared anthracene-urea compounds (9An and 2An), a pyrene-urea compound (Py) and an anthracene-diurea compound (9,10An), which have alkylsulfonyl groups to improve their solubility in various organic solvents. We investigated the solvent effects of the ESIPT reaction using absorption, fluorescence, and 1H NMR spectroscopy along with fluorescence decay measurements in dimethyl sulfoxide (DMSO), acetonitrile (MeCN), tetrahydrofuran (THF) and toluene. The tautomer fluorescence of 9An showed remarkable solvent dependence on the spectral red-shift compared with 2An, Py and 9,10An. As a result of the detailed spectroscopic investigations with regard to the solvent including kinetic analysis of the ESIPT for 9AnAcO-, we revealed that the energy gap between the normal and tautomer forms in the excited state depended on the hydrogen bond acceptor basicity (β), which is one of the Kamlet-Taft solvent parameters. Finally, we discovered that the tautomer structures of aromatic-urea compounds were stabilized by hydrogen bond interactions.

[1]  Y. Nishimura,et al.  Fluorescence Sensor with A New ON1–OFF–ON2 Switching Mechanism Using the Excited State Intermolecular Proton Transfer Reaction of An Anthracene‐diurea Compound , 2017, Photochemistry and photobiology.

[2]  Y. Nishimura,et al.  Excited-state intermolecular proton transfer dependent on the substitution pattern of anthracene-diurea compounds involved in fluorescent ON1-OFF-ON2 response by the addition of acetate ions. , 2017, Organic & biomolecular chemistry.

[3]  Ling‐Kang Liu,et al.  Solvatochromic photoluminescence investigation of functional Schiff-bases: A systematic study of substituent effects , 2017 .

[4]  A. Misra,et al.  Photoenolization via excited state proton transfer and ion sensing studies of hydroxy imidazole derivatives , 2017 .

[5]  M. C. Kroon,et al.  Ionic liquids and deep eutectic solvents for lignocellulosic biomass fractionation. , 2017, Physical chemistry chemical physics : PCCP.

[6]  Y. Nishimura,et al.  Control of the intermolecular photodimerization of anthracene derivatives by hydrogen bonding of urea groups in dilute solution , 2016, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[7]  T. Welton,et al.  Determination of Kamlet-Taft parameters for selected solvate ionic liquids. , 2016, Physical chemistry chemical physics : PCCP.

[8]  Tomoo Sato,et al.  Producing a dual-fluorescent molecule by tuning the energetics of excited-state intramolecular proton transfer , 2015, Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology.

[9]  N. Basarić,et al.  Anion binding with urea and thiourea derivatives , 2015 .

[10]  H. Singh,et al.  Triple-signaling mechanisms-based three-in-one multi-channel chemosensor for discriminating Cu2+, acetate and ion pair mimicking AND, NOR, INH and IMP logic functions , 2015 .

[11]  Y. Nishimura,et al.  Aggregated Excimer Formation through Hydrogen Bonding in a Pyrene–Urea Derivative , 2015 .

[12]  Baodui Wang,et al.  4-(8′-Hydroxyquinolin-7′-yl)methyleneimino-1-phenyl-2,3-dimethyl-5-pyzole as a fluorescent chemosensor for aluminum ion in acid aqueous medium , 2014 .

[13]  S. Irle,et al.  A strap strategy for construction of an excited-state intramolecular proton transfer (ESIPT) system with dual fluorescence. , 2014, Angewandte Chemie.

[14]  Ge Liu,et al.  Ratiometric fluorescence anion sensor based on inhibition of excited-state intramolecular proton transfer (ESIPT) , 2014, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[15]  S. Goswami,et al.  Remarkable ESIPT induced NIR emission by a selective colorimetric dibenzimidazolo diimine sensor for acetate , 2013 .

[16]  S. Goswami,et al.  Competitive intra- and inter-molecular proton transfer in hydroxynaphthyl benzothiazole: selective ratiometric sensing of acetate , 2013 .

[17]  G. Bergamaschi,et al.  The interaction of fluoride with fluorogenic ureas: an ON1-OFF-ON2 response. , 2013, Journal of the American Chemical Society.

[18]  P. Chou,et al.  Excited-state proton coupled charge transfer modulated by molecular structure and media polarization. , 2013, Chemical Society reviews.

[19]  Ge Liu,et al.  Ratiometric fluorescence and colorimetric sensing of anion utilizing simple Schiff base derivatives , 2013, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[20]  Y. Nishimura,et al.  Kinetic analysis of photoinduced reactions in hydrogen-bonded complexes of anthracene-urea with anions , 2012 .

[21]  J. Jayabharathi,et al.  Potential fluorescent chemosensor based on L-tryptophan derivative: DFT based ESIPT process. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[22]  W. Thiel,et al.  Intramolecular hydrogen bonding plays a crucial role in the photophysics and photochemistry of the GFP chromophore. , 2012, Journal of the American Chemical Society.

[23]  P. Chou,et al.  Fine tuning the energetics of excited-state intramolecular proton transfer (ESIPT): white light generation in a single ESIPT system. , 2011, Journal of the American Chemical Society.

[24]  Y. Nishimura,et al.  Kinetics of hydrogen bonding between anthracene urea derivatives and anions in the excited state. , 2011, The journal of physical chemistry. A.

[25]  Y. Nishimura,et al.  Kinetic studies of emissive guanine derivatives bearing anthracene moiety , 2011 .

[26]  Luigi Fabbrizzi,et al.  Anion recognition by hydrogen bonding: urea-based receptors. , 2010, Chemical Society reviews.

[27]  Bijan Kumar Paul,et al.  Modulated photophysics of an ESIPT probe 1-hydroxy-2-naphthaldehyde within motionally restricted environments of liposome membranes having varying surface charges. , 2010, The journal of physical chemistry. B.

[28]  Hong-Seok Kim,et al.  Thiazole-based chemosensor III: synthesis and fluorescence sensing of CH3CO2− based on inhibition of ESIPT , 2010 .

[29]  S. Canuto,et al.  Solvent effects in chemical processes. water-assisted proton transfer reaction of pterin in aqueous environment. , 2009, The journal of physical chemistry. A.

[30]  Se Hun Kim,et al.  A white-light-emitting molecule: frustrated energy transfer between constituent emitting centers. , 2009, Journal of the American Chemical Society.

[31]  Wenhao Sun,et al.  Understanding solvent effects on luminescent properties of a triple fluorescent ESIPT compound and application for white light emission. , 2009, The journal of physical chemistry. A.

[32]  J. Catalán.  Toward a generalized treatment of the solvent effect based on four empirical scales: dipolarity (SdP, a new scale), polarizability (SP), acidity (SA), and basicity (SB) of the medium. , 2009, The journal of physical chemistry. B.

[33]  A. Secchi,et al.  Design, Synthesis and Recognition Properties of Urea-Type Anion Receptors in Low Polar Media , 2008 .

[34]  M. Ikegami,et al.  Photochemical Behavior of an Anthracene–Urea Derivative Interacting with Anions , 2007 .

[35]  M. Ikegami,et al.  The relaxation dynamics of the excited state of stilbene dendrimers substituted with phenylacetylene groups , 2006 .

[36]  F. Rodembusch,et al.  New fluorescent monomers and polymers displaying an intramolecular proton-transfer mechanism in the electronically excited state (esipt). IV. Synthesis of acryloylamide and diallylamino benzazole dyes and its copolymerization with MMA , 2006 .

[37]  Sarah J. Schmidtke,et al.  Probing excited-state dynamics and intramolecular proton transfer in 1-acylaminoanthraquinones via the intermolecular solvent response. , 2005, The journal of physical chemistry. A.

[38]  M. Balamurali,et al.  Excited state intramolecular proton transfer in 2-(2′-amino-3-pyridyl)-benzimidazole: effect of solvents , 2004 .

[39]  A. Bader,et al.  Solvent influence on excited-state intramolecular proton transfer in 3-hydroxychromone derivatives studied by cryogenic high-resolution fluorescence spectroscopy. , 2003, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[40]  A. Demchenko,et al.  Multiparametric probing of intermolecular interactions with fluorescent dye exhibiting excited state intramolecular proton transfer , 2003 .

[41]  P. Matousek,et al.  Ultrafast measurements of excited state intramolecular proton transfer (ESIPT) in room temperature solutions of 3-hydroxyflavone and derivatives , 2001 .

[42]  S. Santra,et al.  Excited state intramolecular proton transfer in 2-(2′-benzamidophenyl)benzimidazole: effect of solvents , 1999 .

[43]  S. Tobita,et al.  Effects of Electronic Structures on the Excited-State Intramolecular Proton Transfer of 1-Hydroxy-2-acetonaphthone and Related Compounds , 1998 .

[44]  C. Reichardt,et al.  Solvatochromic Dyes as Solvent Polarity Indicators , 1994 .

[45]  L. Arnaut,et al.  Excited-state proton transfer reactions I. Fundamentals and intermolecular reactions , 1993 .

[46]  B. Malmström,et al.  Cytochrome oxidase as a redox-linked proton pump. , 1990, Acta physiologica Scandinavica. Supplementum.

[47]  N. Chattopadhyay.  Effect of cyclodextrin complexation on excited state proton transfer reactions , 1991 .

[48]  I. Yamazaki,et al.  Picosecond single photon timing measurements with a proximity type microchannel plate photomultiplier and global analysis with reference convolution , 1990 .

[49]  E. S. Mansueto,et al.  Excited-state proton-transfer polymerization of amorphous formaldehyde , 1989 .

[50]  B. Valeur,et al.  Ion-responsive fluorescent compounds. 1. Effect of cation binding on photophysical properties of benzoxazinone derivative linked to monoaza-15-crown-5 , 1988 .

[51]  K. Ghiggino,et al.  Effect of solvent on excited-state intramolecular proton transfer in benzotriazole photostabilizers , 1986 .

[52]  M. Politi,et al.  Water activity in reversed sodium bis(2-ethylhexyl) sulfosuccinate micelles , 1986 .

[53]  H. Shioyama,et al.  Behavior of radical ion pairs produced by photoinduced electron transfer in polar solutions : Their dynamics in picosecond-hundred nanosecond regime , 1986 .

[54]  D. Mcmorrow,et al.  The proton-transfer laser. Gain spectrum and amplification of spontaneous emission of 3-hydroxyflavone , 1984 .

[55]  Michael H. Abraham,et al.  LINEAR SOLVATION ENERGY RELATIONSHIPS. 23. A COMPREHENSIVE COLLECTION OF THE SOLVATOCHROMIC PARAMETERS, Π*, α, AND β, AND SOME METHODS FOR SIMPLIFYING THE GENERALIZED SOLVATOCHROMIC EQUATION , 1984 .

[56]  Michael H. Abraham,et al.  Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, .pi.*, .alpha., and .beta., and some methods for simplifying the generalized solvatochromic equation , 1983 .

[57]  D. Mcmorrow,et al.  Proton-transfer spectroscopy of 3-hydroxychromones: extreme sensitivity to hydrogen-bonding perturbations , 1983 .

[58]  N. Mataga,et al.  Picosecond laser spectroscopy of intramolecular heteroexcimer systems. Time-resolved absorption studies of p-(CH3)2NC6H4(CH2)n-1-pyrenyl and 9-anthryl systems , 1981 .

[59]  R. Taft,et al.  Linear solvation energy relationships Solvent effects on some fluorescence probes , 1981 .

[60]  R. Taft,et al.  Solvatochromic comparison methods. 13. Linear solvation energy relationship. 5. Correlations between infrared .DELTA..nu. values and the .beta. scale of hydrogen bond acceptor basicities , 1979 .

[61]  K. R. Winn,et al.  Picosecond studies of excited-state protonation and deprotonation kinetics. The laser pH jump , 1979 .

[62]  N. Mataga,et al.  Solvent Effects upon Dynamic Behavior of Intramolecular Heteroexcimers , 1977 .

[63]  R. Taft,et al.  The solvatochromic comparison method. 2. The .alpha.-scale of solvent hydrogen-bond donor (HBD) acidities , 1976 .

[64]  R. Taft,et al.  The solvatochromic comparison method. I. The .beta.-scale of solvent hydrogen-bond acceptor (HBA) basicities , 1976 .

[65]  K. Ninomiya,et al.  Phosphorus in organic synthesis—VII , 1974 .

[66]  L. Brand,et al.  Excited-state proton transfer as a biological probe. Determination of rate constants by means of nanosecond fluorometry. , 1972, Biochemistry.

[67]  Rudolph A. Marcus,et al.  On the Theory of Oxidation‐Reduction Reactions Involving Electron Transfer. I , 1956 .

[68]  N. Mataga,et al.  The Solvent Effect on Fluorescence Spectrum, Change of Solute-Solvent Interaction during the Lifetime of Excited Solute Molecule , 1955 .

[69]  Ernst Lippert,et al.  Dipolmoment und Elektronenstruktur von angeregten Molekülen , 1955 .