메뉴 건너뛰기




Volumn 216, Issue 1, 2010, Pages 24-34

Unusual large Stokes shift and solvatochromic fluorophore: Synthesis, spectra, and solvent effect of 6-substituted 2,3-naphthalimide

Author keywords

6 Substituted 2,3 naphthalimide; Environment sensitive fluorophore; Large Stokes shift; Photophysics; Solvent effect

Indexed keywords


EID: 77958461202     PISSN: 10106030     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochem.2010.09.002     Document Type: Article
Times cited : (31)

References (33)
  • 1
    • 0001462978 scopus 로고    scopus 로고
    • 4-Aminophthalimide derivatives as environment sensitive probes
    • G. Saroja, T. Soujanya, B. Ramachandram, and A. Samanta 4-Aminophthalimide derivatives as environment sensitive probes J. Fluoresc. 119 1998 405 410
    • (1998) J. Fluoresc. , vol.119 , pp. 405-410
    • Saroja, G.1    Soujanya, T.2    Ramachandram, B.3    Samanta, A.4
  • 2
    • 0018786922 scopus 로고
    • Synthesis and spectral properties of a hydrophobic fluorescent probe: 2-dimethylamino-6-propionylnaphthalene
    • G. Weber, and F.J. Farris Synthesis and spectral properties of a hydrophobic fluorescent probe: 2-dimethylamino-6-propionylnaphthalene Biochemistry 18 1979 3075 3078
    • (1979) Biochemistry , vol.18 , pp. 3075-3078
    • Weber, G.1    Farris, F.J.2
  • 3
    • 53849106505 scopus 로고    scopus 로고
    • A versatile amino acid analogue of the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide: A powerful tool for the study of dynamic protein interactions
    • G. Loving, and B. Imperiali A versatile amino acid analogue of the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide: a powerful tool for the study of dynamic protein interactions J. Am. Chem. Soc. 130 2008 13630 13638
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 13630-13638
    • Loving, G.1    Imperiali, B.2
  • 4
    • 59849116051 scopus 로고    scopus 로고
    • Fluorescent amino acids: Advances in protein-extrinsic fluorophores
    • R.K. Alan, and N. Tamari Fluorescent amino acids: advances in protein-extrinsic fluorophores Org. Biomol. Chem. 7 2009 627 634
    • (2009) Org. Biomol. Chem. , vol.7 , pp. 627-634
    • Alan, R.K.1    Tamari, N.2
  • 5
    • 77958473068 scopus 로고    scopus 로고
    • U.S. Pat. Appl. Publ US 2006234206 A1
    • B. Imperiali, M.E. Vazquez, U.S. Pat. Appl. Publ. 2006, 25pp. US 2006234206 A1.
    • (2006)
    • Imperiali, B.1    Vazquez, M.E.2
  • 6
    • 13644266900 scopus 로고    scopus 로고
    • Photophysics and biological applications of the environment-sensitive fluorophore 6-N,N-dimethylamino-2,3-naphthalimide
    • M.E. Vazquez, J.B. Blanco, and B. Imperiali Photophysics and biological applications of the environment-sensitive fluorophore 6-N,N-dimethylamino-2,3- naphthalimide J. Am. Chem. Soc. 127 2005 1300 1306
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 1300-1306
    • Vazquez, M.E.1    Blanco, J.B.2    Imperiali, B.3
  • 7
    • 77749255351 scopus 로고    scopus 로고
    • Synthesis and fluorescence of the new environment-sensitive fluorophore 6-chloro-2,3-naphthalimide derivative
    • R.K. Alan, S. Ozcana, and E. Todadze Synthesis and fluorescence of the new environment-sensitive fluorophore 6-chloro-2,3-naphthalimide derivative Org. Biomol. Chem. 8 2010 1296 1300
    • (2010) Org. Biomol. Chem. , vol.8 , pp. 1296-1300
    • Alan, R.K.1    Ozcana, S.2    Todadze, E.3
  • 8
    • 74049147038 scopus 로고    scopus 로고
    • Monitoring protein interactions and dynamics with solvatochromic fluorophores
    • G. Loving, M. Sainlos, and B. Imperiali Monitoring protein interactions and dynamics with solvatochromic fluorophores Trends Biotechnol. 28 2010 73 83
    • (2010) Trends Biotechnol. , vol.28 , pp. 73-83
    • Loving, G.1    Sainlos, M.2    Imperiali, B.3
  • 11
    • 7444227388 scopus 로고    scopus 로고
    • A new environment-sensitive fluorescent amino acid for Fmoc-based solid phase peptide synthesis
    • M.E. Vazquez, D.M. Rothman, and B. Imperiali A new environment-sensitive fluorescent amino acid for Fmoc-based solid phase peptide synthesis Org. Biomol. Chem. 2 2004 1965 1966
    • (2004) Org. Biomol. Chem. , vol.2 , pp. 1965-1966
    • Vazquez, M.E.1    Rothman, D.M.2    Imperiali, B.3
  • 12
    • 0036972164 scopus 로고    scopus 로고
    • Enantioselective synthesis and application of the highly fluorescent and environment-sensitive amino acid 6-(2-dimethylamino-naphthoyl) alanine (DANA)
    • M. Nitz, A.R. Mezo, M.H. Ali, and B. Imperiali Enantioselective synthesis and application of the highly fluorescent and environment-sensitive amino acid 6-(2-dimethylamino-naphthoyl) alanine (DANA) Chem. Commun. (Camb.) 2002 1912 1913
    • (2002) Chem. Commun. (Camb.) , pp. 1912-1913
    • Nitz, M.1    Mezo, A.R.2    Ali, M.H.3    Imperiali, B.4
  • 13
    • 0037204951 scopus 로고    scopus 로고
    • Probing protein electrostatics with a synthetic fluorescent amino acid
    • B.E. Cohen Probing protein electrostatics with a synthetic fluorescent amino acid Science 296 2002 1700 1703
    • (2002) Science , vol.296 , pp. 1700-1703
    • Cohen, B.E.1
  • 14
    • 0033611943 scopus 로고    scopus 로고
    • Nucleic acid oxidation mediated by naphthalene and benzophenone imide and diimide derivatives: Consequences for DNA redox chemistry
    • J.E. Rogers, and L.A. Kelly Nucleic acid oxidation mediated by naphthalene and benzophenone imide and diimide derivatives: consequences for DNA redox chemistry J. Am. Chem. Soc. 121 1999 3854 3861
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3854-3861
    • Rogers, J.E.1    Kelly, L.A.2
  • 15
    • 0029056686 scopus 로고
    • Photoactivatable DNA-cleaving amino acids: Highly sequence-selective DNA photocleavage by novel l-lysine derivatives
    • I. Saito, M. Takayama, and S. Kawanishi Photoactivatable DNA-cleaving amino acids: highly sequence-selective DNA photocleavage by novel l-lysine derivatives J. Am. Chem. Soc. 117 1995 5590 5591
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5590-5591
    • Saito, I.1    Takayama, M.2    Kawanishi, S.3
  • 17
    • 0032580424 scopus 로고    scopus 로고
    • A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide
    • F. Cosnard, and V. Wintgens A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide Tetrahedron Lett. 39 1998 2751 2754
    • (1998) Tetrahedron Lett. , vol.39 , pp. 2751-2754
    • Cosnard, F.1    Wintgens, V.2
  • 18
    • 34247095184 scopus 로고    scopus 로고
    • Pyrophosphate-selective fluorescent chemosensor at physiological pH: Formation of a unique excimer upon addition of pyrophosphate
    • H.N. Lee, Z. Xu, S.K. Kim, K.M.K. Swamy, Y. Kim, S.J. Kim, and J. Yoon Pyrophosphate-selective fluorescent chemosensor at physiological pH: formation of a unique excimer upon addition of pyrophosphate J Am. Chem. Soc. 129 2007 3828 3829
    • (2007) J Am. Chem. Soc. , vol.129 , pp. 3828-3829
    • Lee, H.N.1    Xu, Z.2    Kim, S.K.3    Swamy, K.M.K.4    Kim, Y.5    Kim, S.J.6    Yoon, J.7
  • 19
    • 0036248868 scopus 로고    scopus 로고
    • Covalently immobilized aminonaphthalimide as fluorescent carrier for the preparation of optical sensors
    • C.G. Niu, Z.Z. Li, X.B. Zhang, W.Q. Lin, G.L. Shen, and R.Q. Yu Covalently immobilized aminonaphthalimide as fluorescent carrier for the preparation of optical sensors Anal. Bioanal. Chem. 372 2002 519 524
    • (2002) Anal. Bioanal. Chem. , vol.372 , pp. 519-524
    • Niu, C.G.1    Li, Z.Z.2    Zhang, X.B.3    Lin, W.Q.4    Shen, G.L.5    Yu, R.Q.6
  • 20
    • 0000749516 scopus 로고    scopus 로고
    • Comprehensive model of the photophysics of N-phenylnaphthalimides: The role of solvent and rotational relaxation
    • A. Demeter, T. Berces, L. Biczok, V. Wintgens, P. Valat, and J. Kossanyi Comprehensive model of the photophysics of N-phenylnaphthalimides: the role of solvent and rotational relaxation J. Phys. Chem. 100 1996 2001 2011
    • (1996) J. Phys. Chem. , vol.100 , pp. 2001-2011
    • Demeter, A.1    Berces, T.2    Biczok, L.3    Wintgens, V.4    Valat, P.5    Kossanyi, J.6
  • 22
    • 0030600682 scopus 로고    scopus 로고
    • Spectroscopic properties of aromatic dicarboximides part 3: Substituent effect on the photophysical properties of N-phenyl-2,3-napthalimides
    • V. Wintgens, P. Valat, J. Kossanyi, A. Demeter, L. Biczok, and T. Berces Spectroscopic properties of aromatic dicarboximides part 3: substituent effect on the photophysical properties of N-phenyl-2,3-napthalimides J. Photochem. Photobiol. A Chem. 93 1996 109 117
    • (1996) J. Photochem. Photobiol. A Chem. , vol.93 , pp. 109-117
    • Wintgens, V.1    Valat, P.2    Kossanyi, J.3    Demeter, A.4    Biczok, L.5    Berces, T.6
  • 23
    • 0001637448 scopus 로고
    • Spectroscopic properties of aromatic dicarboximides. Part 2: Substituent effect on the photophysical properties of N-phenyl-1,2-naphthalimide
    • A. Demeter, T. Berces, L. Biczok, V. Wintgens, P. Valat, and J. Kossanyi Spectroscopic properties of aromatic dicarboximides. Part 2: substituent effect on the photophysical properties of N-phenyl-1,2-naphthalimide J. Chem. Soc. Faraday Trans. 90 1994 2635 2641
    • (1994) J. Chem. Soc. Faraday Trans. , vol.90 , pp. 2635-2641
    • Demeter, A.1    Berces, T.2    Biczok, L.3    Wintgens, V.4    Valat, P.5    Kossanyi, J.6
  • 24
    • 20844461913 scopus 로고    scopus 로고
    • Matrix screening of substituted N-Aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually bright pyridine derivatives
    • H. Cao, V. Chang, R. Hernandez, and M.D. Heagy Matrix screening of substituted N-Aryl-1,8-naphthalimides reveals new dual fluorescent dyes and unusually bright pyridine derivatives J. Org. Chem. 70 2005 4929 4934
    • (2005) J. Org. Chem. , vol.70 , pp. 4929-4934
    • Cao, H.1    Chang, V.2    Hernandez, R.3    Heagy, M.D.4
  • 25
  • 26
    • 0242636463 scopus 로고    scopus 로고
    • Synthesis and hypolipidemic activity of N-substituted phthalimides part v
    • V.M. Sena, R.M. Srivastava, and R.O. Silva Synthesis and hypolipidemic activity of N-substituted phthalimides part V IL Farmaco 58 2003 1283 1288
    • (2003) IL Farmaco , vol.58 , pp. 1283-1288
    • Sena, V.M.1    Srivastava, R.M.2    Silva, R.O.3
  • 27
    • 84941384717 scopus 로고
    • Dipole moment and electronic structure of excited molecules
    • E. Lippert, and Z. Naturforsch Dipole moment and electronic structure of excited molecules Phys. Sci. A 10 1955 541 545
    • (1955) Phys. Sci. A , vol.10 , pp. 541-545
    • Lippert, E.1    Naturforsch, Z.2
  • 28
    • 0035892187 scopus 로고    scopus 로고
    • Radiationless deactivation of an intramolecular charge transfer excited state through hydrogen bonding: Effect of molecular structure and hard-soft anionic character in the excited state
    • A. Morimoto, T. Yatsuhashi, T. Shimada, L. Biczok, D.A. Tryk, and H. Inoue Radiationless deactivation of an intramolecular charge transfer excited state through hydrogen bonding: effect of molecular structure and hard-soft anionic character in the excited state J. Phys. Chem. A 105 2001 10488 10496
    • (2001) J. Phys. Chem. A , vol.105 , pp. 10488-10496
    • Morimoto, A.1    Yatsuhashi, T.2    Shimada, T.3    Biczok, L.4    Tryk, D.A.5    Inoue, H.6
  • 29
    • 77954252179 scopus 로고    scopus 로고
    • Time-dependent density functional theory study on the electronic excited-state hydrogen-bonding dynamics of 4-aminophthalimide (4AP) in aqueous solution: 4AP and 4AP-(H(2)O)(1,2) clusters
    • R. Wang, C. Hao, P. Li, N.N. Wei, J. Chen, and J. Qiu Time-dependent density functional theory study on the electronic excited-state hydrogen-bonding dynamics of 4-aminophthalimide (4AP) in aqueous solution: 4AP and 4AP-(H(2)O)(1,2) clusters J. Comput. Chem. 31 2010 2157 2163
    • (2010) J. Comput. Chem. , vol.31 , pp. 2157-2163
    • Wang, R.1    Hao, C.2    Li, P.3    Wei, N.N.4    Chen, J.5    Qiu, J.6
  • 30
    • 0036784570 scopus 로고    scopus 로고
    • Infrared-optical double-resonance measurements of hydrogen-bonded interactions in clusters involving aminophthalimides
    • Y. Chen, and M.R. Topp Infrared-optical double-resonance measurements of hydrogen-bonded interactions in clusters involving aminophthalimides Chem. Phys. 283 2002 249 268
    • (2002) Chem. Phys. , vol.283 , pp. 249-268
    • Chen, Y.1    Topp, M.R.2
  • 32
    • 0000656957 scopus 로고
    • New derivatizing agents for amino acids and peptides. I: Facile synthesis of N-substituted 1-cyanobenz[f]isoindoles and their spectroscopic properties
    • R.G. Carlson, K. Srinivasachar, R.S. Givens, and B.K. Matuszewski New derivatizing agents for amino acids and peptides. I: facile synthesis of N-substituted 1-cyanobenz[f]isoindoles and their spectroscopic properties J. Org. Chem. 51 1986 3978 3983
    • (1986) J. Org. Chem. , vol.51 , pp. 3978-3983
    • Carlson, R.G.1    Srinivasachar, K.2    Givens, R.S.3    Matuszewski, B.K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.