Study on the synthesis and structure-effect relationship of multi-aryl imidazoles with their fluorescence properties.

In this paper, 23 multi-aryl imidazole derivatives were synthesized and identified by nuclear magnetic resonance, ultraviolet-visible and elemental analysis. At the same time, their ultraviolet-visible maximum absorption (λ(ab)(max)), fluorescence emission maximum (λ(em)(max)) and quantum yields (Ф(f)) were measured. The relationships between the optical behaviors and structures for these compounds were assessed. The results show that the λ(max)(ab) and λ(max)(em) are red-shifted and the fluorescence Ф(f) are increased by the introduction of electron-withdrawing substituents and the increase in the planarity of multi-aryl imidazole molecules. The results also showed that the fluorescence quantum yields of the compounds containing two imidazole nuclei are double the corresponding mono-imidazole nucleus compounds.

[1]  J. Lupton.  Chromophores in conjugated polymers--all straight? , 2012, Chemphyschem : a European journal of chemical physics and physical chemistry.

[2]  J. Jayabharathi,et al.  Physicochemical studies of some novel Y-shaped imidazole derivatives--a sensitive chemisensor. , 2011, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[3]  Soo Young Park,et al.  Advanced Organic Optoelectronic Materials: Harnessing Excited‐State Intramolecular Proton Transfer (ESIPT) Process , 2011, Advanced materials.

[4]  F. Shibahara,et al.  1-Alkynyl- and 1-alkenyl-3-arylimidazo[1,5-a]pyridines: synthesis, photophysical properties, and observation of a linear correlation between the fluorescent wavelength and Hammett substituent constants. , 2011, The Journal of organic chemistry.

[5]  L. Antonov,et al.  Aggregation of 2-aminobenzimidazole--a combined experimental and theoretical investigation. , 2011, Chemphyschem : a European journal of chemical physics and physical chemistry.

[6]  Haixia Lin,et al.  New fluorene derivatives based on 3,9-dihydrofluoreno[3,2-d]imidazole (FI): Characterization and influence of substituents on photoluminescence , 2011 .

[7]  Weiting Liao,et al.  (E)-Ethyl 2-cyano-3-[4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl]acrylate dihydrate , 2011, Acta crystallographica. Section E, Structure reports online.

[8]  Mao-Sen Yuan,et al.  Switching high two-photon efficiency: from 3,8,13-substituted triindole derivatives to their 2,7,12-isomers. , 2010, Organic letters.

[9]  T. Hiyama,et al.  Organic fluorophores exhibiting highly efficient photoluminescence in the solid state. , 2010, Chemistry, an Asian journal.

[10]  S. Manoharan,et al.  Specificity and Selectivity in Photoluminescent Properties of π-Conjugated Benzheterazole Molecules , 2009 .

[11]  Y. Ooyama,et al.  Photophysical properties of phenanthro[9,10-d]imidazole-type fluorescent hosts upon inclusion of organic solvent molecules , 2009 .

[12]  Dan-yan Lin,et al.  Synthesis and optical behaviors of 2-(9-phenanthrenyl)-, 2-(9-anthryl)-, and 2-(1-pyrenyl)-1-alkylimidazole homologues. , 2009, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[13]  P. Sonar,et al.  Electron-accepting conjugated materials based on 2-vinyl-4,5-dicyanoimidazoles for application in organic electronics. , 2009, The Journal of organic chemistry.

[14]  M. Gross,et al.  Balance of beneficial and deleterious health effects of quinones: a case study of the chemical properties of genistein and estrone quinones. , 2009, Journal of the American Chemical Society.

[15]  Lin Yuan,et al.  Construction of fluorescent probes via protection/deprotection of functional groups: a ratiometric fluorescent probe for Cu2+. , 2009, Chemistry.

[16]  Lin Yuan,et al.  A ratiometric fluorescent probe for cysteine and homocysteine displaying a large emission shift. , 2008, Organic Letters.

[17]  Martin Matschke,et al.  4H-Imidazoles as functional dyes: synthesis of bichromophores and extension of the merocyanine system , 2008 .

[18]  K. Burgess,et al.  Syntheses of highly fluorescent GFP-chromophore analogues. , 2008, Journal of the American Chemical Society.

[19]  J. Shear,et al.  Modular fluorescent benzobis(imidazolium) salts: syntheses, photophysical analyses, and applications. , 2008, Journal of the American Chemical Society.

[20]  Andrew J Boydston,et al.  Phase-tunable fluorophores based upon benzobis(imidazolium) salts. , 2007, Journal of the American Chemical Society.

[21]  S. Speiser,et al.  Structures and photophysics of lophine and double lophine derivatives , 2007 .

[22]  Nan Xie,et al.  Synthesis and photophysical properties of 1,4-bis(4,5-diarylimidazol) benzene dyes , 2007 .

[23]  C. Fahrni,et al.  Excited-state intramolecular proton transfer in 2-(2'-arylsulfonamidophenyl)benzimidazole derivatives: the effect of donor and acceptor substituents. , 2007, The Journal of organic chemistry.

[24]  Y. Eichen,et al.  Spectroscopy, photophysical and photochemical properties of bisimidazole derivatives , 2007 .

[25]  Jie-ying Wu,et al.  Synthesis, luminescence and cyclic voltammetric studies of several novel carboxylato diruthenium complexes , 2007 .

[26]  Kiyoshi Tanaka,et al.  Fluorescent behavior of 2-(3,4,5,6-tetrafluoro-2-hydroxyphenyl)imidazo-[1,2-a]pyridine in the presence of metal perchlorate , 2007 .

[27]  M. Nayak,et al.  Spectral characteristics of various prototropic species of 2-(3′-aminophenyl)pyrido[3,4-d]imidazole , 2005 .

[28]  K. Feng,et al.  Tuning fluorescence properties of imidazole derivatives with thiophene and thiazole , 2004 .

[29]  V. Karachevtsev,et al.  Absorption and fluorescent spectral studies of imidazophenazine derivatives. , 2004, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[30]  Katsuhira Yoshida,et al.  Crystallographic structure and solid-state fluorescence enhancement behavior of a 2-(9-anthryl)phenanthroimidazole-type clathrate host upon inclusion of amine molecules , 2003 .

[31]  L. Ji,et al.  A fluorescence study of tetraphenylporphyrinatozinc(II)/imidazolyl-linked porphyrinatoiron(III) systems. , 2003, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[32]  Katsuhira Yoshida,et al.  Crystallographic structures and solid fluorescence behaviors of crystals of a 2-(9-anthryl)phenanthroimidazole-type clathrate host , 2003 .

[33]  A. N. Petrukhin,et al.  Spectral luminescent properties and dynamics of intramolecular processes in 2,4,5-triarylimidazoles , 2003 .

[34]  E. Moran,et al.  2,4,5-Trisubstituted imidazoles: novel nontoxic modulators of P-glycoprotein mediated multidrug resistance. Part 1. , 2000, Bioorganic & medicinal chemistry letters.

[35]  Yuexing Zhang,et al.  Organic Semiconductors of Phthalocyanine Compounds for Field Effect Transistors (FETs) , 2010 .

[36]  Huacan Song,et al.  The synthesis and preliminary optical study of 1-alkyl-2,4,5-triphenylimidazole derivatives , 2008 .

[37]  B. Das,et al.  Efficient (bromodimethyl)sulfonium bromide mediated synthesis of benzimidazoles , 2007 .