메뉴 건너뛰기




Volumn 19, Issue 1, 2009, Pages 127-139

Design and synthesis of highly photostable yellow-green emitting 1,8-naphthalimides as fluorescent sensors for metal cations and protons

Author keywords

1,8 Naphthalimide; Fluorescence; Hindered amine light stabilizers; Metal and proton sensors; Photoinduced electron transfer; Photostability

Indexed keywords

1,8-NAPHTHALIMIDE; HINDERED AMINE LIGHT STABILIZERS; METAL AND PROTON SENSORS; PHOTOINDUCED ELECTRON TRANSFER; PHOTOSTABILITY;

EID: 59849119820     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-008-0394-2     Document Type: Article
Times cited : (73)

References (50)
  • 1
    • 0344722565 scopus 로고    scopus 로고
    • Photochemical molecular devices
    • V Balzani 2003 Photochemical molecular devices Photochem Photobiol Sci 2 459 476
    • (2003) Photochem Photobiol Sci , vol.2 , pp. 459-476
    • Balzani, V.1
  • 2
    • 0033830295 scopus 로고    scopus 로고
    • Combining luminescence, coordination and electron transfer for signalling purposes
    • A de Silva D Fox A Huxley T Moody 2000 Combining luminescence, coordination and electron transfer for signalling purposes Coord Chem Rev 205 41 57
    • (2000) Coord Chem Rev , vol.205 , pp. 41-57
    • De Silva, A.1    Fox, D.2    Huxley, A.3    Moody, T.4
  • 3
    • 0035983127 scopus 로고    scopus 로고
    • Rigidization, preorientation and electronic decoupling-the magic triangle for the design of highly efficient fluorescent sensors and switches
    • K Rurack U Resch-Gender 2002 Rigidization, preorientation and electronic decoupling-the magic triangle for the design of highly efficient fluorescent sensors and switches Chem Soc Rev 31 116 127
    • (2002) Chem Soc Rev , vol.31 , pp. 116-127
    • Rurack, K.1    Resch-Gender, U.2
  • 5
    • 0037128543 scopus 로고    scopus 로고
    • Digital processing and communication with molecular switches
    • F Raymo 2002 Digital processing and communication with molecular switches Adv Mater 14 401 414
    • (2002) Adv Mater , vol.14 , pp. 401-414
    • Raymo, F.1
  • 6
    • 0037312758 scopus 로고    scopus 로고
    • A fluorescent chemosensor for sodium based on photoinduced electron transfer
    • H He M Mortellaro M Leiner S Young R Fraatz J Tusa 2003 A fluorescent chemosensor for sodium based on photoinduced electron transfer Anal Chem 75 549 555
    • (2003) Anal Chem , vol.75 , pp. 549-555
    • He, H.1    Mortellaro, M.2    Leiner, M.3    Young, S.4    Fraatz, R.5    Tusa, J.6
  • 7
    • 0037043036 scopus 로고    scopus 로고
    • A novel fluorescent photoinduced electron transfer (PET) sensor for lithium
    • T Gunnlaugsson B Bichell C Nolan 2002 A novel fluorescent photoinduced electron transfer (PET) sensor for lithium Tetrahedron Lett 43 4989 4992
    • (2002) Tetrahedron Lett , vol.43 , pp. 4989-4992
    • Gunnlaugsson, T.1    Bichell, B.2    Nolan, C.3
  • 8
    • 11944261083 scopus 로고
    • Molecular fluorescent signalling with fluorophore-spacer-receptor systems: Approaches to sensing and switching devices via supramolecular photophysics
    • R Bissell A de Silva H Gunaratne P Lynch G Maguire C McCoy 1992 Molecular fluorescent signalling with fluorophore-spacer-receptor systems: approaches to sensing and switching devices via supramolecular photophysics Chem Soc Rev 21 187 196
    • (1992) Chem Soc Rev , vol.21 , pp. 187-196
    • Bissell, R.1    De Silva, A.2    Gunaratne, H.3    Lynch, P.4    Maguire, G.5    McCoy, C.6
  • 10
    • 0033835907 scopus 로고    scopus 로고
    • Design principles of fluorescent molecular sensors for cation recognition
    • B Valeur I Leray 2000 Design principles of fluorescent molecular sensors for cation recognition Coord Chem Rev 205 3 40
    • (2000) Coord Chem Rev , vol.205 , pp. 3-40
    • Valeur, B.1    Leray, I.2
  • 12
    • 9644263229 scopus 로고    scopus 로고
    • Newer optical based molecular devices from older coordination chemistry
    • A de Silva B McCaughan B McKinney M Querol 2003 Newer optical based molecular devices from older coordination chemistry Dalton Transactions 10 1902 1913
    • (2003) Dalton Transactions , vol.10 , pp. 1902-1913
    • De Silva, A.1    McCaughan, B.2    McKinney, B.3    Querol, M.4
  • 13
    • 23644444124 scopus 로고    scopus 로고
    • Luminescent sensors and switches in the early 21st century
    • J Callan A de Silva D Magri 2005 Luminescent sensors and switches in the early 21st century Tetrahedron 61 8551 8588
    • (2005) Tetrahedron , vol.61 , pp. 8551-8588
    • Callan, J.1    De Silva, A.2    Magri, D.3
  • 14
    • 0037380168 scopus 로고    scopus 로고
    • Luminescent properties and photo-induced electron transfer of naphthalimides with piperazine substituent
    • J Gan K Chen CP Chang H Tian 2003 Luminescent properties and photo-induced electron transfer of naphthalimides with piperazine substituent Dyes Pigm 57 21 28
    • (2003) Dyes Pigm , vol.57 , pp. 21-28
    • Gan, J.1    Chen, K.2    Chang, C.P.3    Tian, H.4
  • 15
    • 3242678723 scopus 로고    scopus 로고
    • The pH-dependent fluorescence of pyridylmethyl-4-amino-1,8-naphthalimides
    • A de Silva A Goligher H Gunaratne T Rice 2003 The pH-dependent fluorescence of pyridylmethyl-4-amino-1,8-naphthalimides Arkivoc 7 229 243
    • (2003) Arkivoc , vol.7 , pp. 229-243
    • De Silva, A.1    Goligher, A.2    Gunaratne, H.3    Rice, T.4
  • 16
    • 0036853714 scopus 로고    scopus 로고
    • Synthesis of some polymerisable fluorescent dyes
    • L Patrick A Whiting 2002 Synthesis of some polymerisable fluorescent dyes Dyes Pigm 55 123 132
    • (2002) Dyes Pigm , vol.55 , pp. 123-132
    • Patrick, L.1    Whiting, A.2
  • 17
    • 0036736962 scopus 로고    scopus 로고
    • Synthesis of polymerizable 1,8-naphthalimide dyes containing hindered amine fragment
    • V Bojinov T Konstantinova 2002 Synthesis of polymerizable 1,8-naphthalimide dyes containing hindered amine fragment Dyes Pigm 54 239 245
    • (2002) Dyes Pigm , vol.54 , pp. 239-245
    • Bojinov, V.1    Konstantinova, T.2
  • 18
    • 0141576697 scopus 로고    scopus 로고
    • Synthesis of new polymerizable 1,8-naphthalimide dyes containing a 2-hydroxyphenylbenzotriazole fragment
    • V Bojinov I Grabchev 2003 Synthesis of new polymerizable 1,8-naphthalimide dyes containing a 2-hydroxyphenylbenzotriazole fragment Dyes Pigm 59 277 283
    • (2003) Dyes Pigm , vol.59 , pp. 277-283
    • Bojinov, V.1    Grabchev, I.2
  • 19
    • 33847320174 scopus 로고    scopus 로고
    • Synthesis and absorption properties of new yellow-green emitting benzo[de]isoquinoline-1,3-diones containing hindered amine and 2-hydroxyphenylbenzotriazole fragments
    • V Bojinov I Panova 2007 Synthesis and absorption properties of new yellow-green emitting benzo[de]isoquinoline-1,3-diones containing hindered amine and 2-hydroxyphenylbenzotriazole fragments Dyes Pigm 74 551 560
    • (2007) Dyes Pigm , vol.74 , pp. 551-560
    • Bojinov, V.1    Panova, I.2
  • 20
    • 0032583718 scopus 로고    scopus 로고
    • Spectral characteristics and photochemical stability of fluorescence probes based on 1,8-naphthaleneimide in solution and in polymer matrix
    • P Hrdlovič Š Chmela M Danko 1998 Spectral characteristics and photochemical stability of fluorescence probes based on 1,8-naphthaleneimide in solution and in polymer matrix J Photochem Photobiol A Chem 112 197 203
    • (1998) J Photochem Photobiol A Chem , vol.112 , pp. 197-203
    • Hrdlovič, P.1    Chmela, Š.2    Danko, M.3
  • 21
    • 39149101794 scopus 로고    scopus 로고
    • Synthesis and spectral characteristics of di-substituted 1,8-naphthalimides: Bi-radical formation
    • J Kollar P Hrdlovič Š Chmela 2008 Synthesis and spectral characteristics of di-substituted 1,8-naphthalimides: bi-radical formation J Photochem Photobiol A Chem 195 64 71
    • (2008) J Photochem Photobiol A Chem , vol.195 , pp. 64-71
    • Kollar, J.1    Hrdlovič, P.2    Chmela, Š.3
  • 22
    • 40549111344 scopus 로고    scopus 로고
    • Spectral properties of probes containing benzothioxanthene chromophore linked with hindered amine in solution and in polymer matrices
    • P Hrdlovič Š Chmela M Danko M Sarakha G Guyot 2008 Spectral properties of probes containing benzothioxanthene chromophore linked with hindered amine in solution and in polymer matrices J Fluoresc 18 393 402
    • (2008) J Fluoresc , vol.18 , pp. 393-402
    • Hrdlovič, P.1    Chmela, Š.2    Danko, M.3    Sarakha, M.4    Guyot, G.5
  • 23
    • 0030148172 scopus 로고    scopus 로고
    • Solvent dependence of the inhibition of intramolecular charge-transfer in N-substituted 1,8-naphthalimide derivatives as dye lasers
    • E Martin R Weigand A Pardo 1996 Solvent dependence of the inhibition of intramolecular charge-transfer in N-substituted 1,8-naphthalimide derivatives as dye lasers J Lumin 68 157 164
    • (1996) J Lumin , vol.68 , pp. 157-164
    • Martin, E.1    Weigand, R.2    Pardo, A.3
  • 24
    • 13444281569 scopus 로고    scopus 로고
    • Spectra of lasing efficiency in lasers with solutions of complex organic compounds
    • V Gruzinskii A Kukhto G Shakkah 1998 Spectra of lasing efficiency in lasers with solutions of complex organic compounds J Appl Spectrosc 65 463 465
    • (1998) J Appl Spectrosc , vol.65 , pp. 463-465
    • Gruzinskii, V.1    Kukhto, A.2    Shakkah, G.3
  • 25
    • 0033169591 scopus 로고    scopus 로고
    • Naphthalimide hydroperoxides as photonucleases: Substituent effects and structural basis
    • ZF Tao X Qian 1999 Naphthalimide hydroperoxides as photonucleases: substituent effects and structural basis Dyes Pigm 43 139 145
    • (1999) Dyes Pigm , vol.43 , pp. 139-145
    • Tao, Z.F.1    Qian, X.2
  • 26
    • 0000308352 scopus 로고
    • Synthesis of 3,6-disulfonated 4-aminonaphthalimides
    • W Stewart 1981 Synthesis of 3,6-disulfonated 4-aminonaphthalimides J Am Chem Soc 103 7615 7620
    • (1981) J Am Chem Soc , vol.103 , pp. 7615-7620
    • Stewart, W.1
  • 28
    • 0032108919 scopus 로고    scopus 로고
    • Luminescent properties of copolymeric dyad compounds containing 1,8-naphthalimide and 1,3,4-oxadiazole
    • W Zhu C Hu K Chen H Tian 1998 Luminescent properties of copolymeric dyad compounds containing 1,8-naphthalimide and 1,3,4-oxadiazole Synth Met 96 151 154
    • (1998) Synth Met , vol.96 , pp. 151-154
    • Zhu, W.1    Hu, C.2    Chen, K.3    Tian, H.4
  • 29
    • 0036092251 scopus 로고    scopus 로고
    • Positive and negative fluorescent imaging induced by naphthalimide polymers
    • H Tian J Gan K Chen J He Q Song X Hou 2002 Positive and negative fluorescent imaging induced by naphthalimide polymers J Mater Chem 12 1262 1267
    • (2002) J Mater Chem , vol.12 , pp. 1262-1267
    • Tian, H.1    Gan, J.2    Chen, K.3    He, J.4    Song, Q.5    Hou, X.6
  • 30
    • 0037162829 scopus 로고    scopus 로고
    • Synthesis and photophysical properties of 1,8-naphthalimide-labelled dendrimers as PET sensors of proton and transition metal ion
    • I Grabchev X Qian V Bojinov Y Xiao W Zhang 2002 Synthesis and photophysical properties of 1,8-naphthalimide-labelled dendrimers as PET sensors of proton and transition metal ion Polymer (Guildf) 43 5731 5736
    • (2002) Polymer (Guildf) , vol.43 , pp. 5731-5736
    • Grabchev, I.1    Qian, X.2    Bojinov, V.3    Xiao, Y.4    Zhang, W.5
  • 31
    • 0042134466 scopus 로고    scopus 로고
    • Two-path photo-induced electron transfer in naphthalimide-based model compound
    • H Tian T Xu Y Zhao K Chen 1999 Two-path photo-induced electron transfer in naphthalimide-based model compound J Chem Soc Perkin Trans 2 545 549
    • (1999) J Chem Soc Perkin Trans , vol.2 , pp. 545-549
    • Tian, H.1    Xu, T.2    Zhao, Y.3    Chen, K.4
  • 32
    • 34247567024 scopus 로고    scopus 로고
    • Fluorescent 4-(2,2,6,6-tetramethylpiperidin-4-ylamino)-1,8-naphthalimide pH chemosensor based on photoinduced electron transfer
    • V Bojinov T Konstantinova 2007 Fluorescent 4-(2,2,6,6- tetramethylpiperidin-4-ylamino)-1,8-naphthalimide pH chemosensor based on photoinduced electron transfer Sens Actuators B Chem 123 869 876
    • (2007) Sens Actuators B Chem , vol.123 , pp. 869-876
    • Bojinov, V.1    Konstantinova, T.2
  • 33
    • 0034291664 scopus 로고    scopus 로고
    • Fluorescence switching in 4-amino-1,8-naphthalimides: "on-off-on" operation controlled by solvent and cations
    • X Poteau A Brown R Brown C Holmes D Matthew 2000 Fluorescence switching in 4-amino-1,8-naphthalimides: "on-off-on" operation controlled by solvent and cations Dyes Pigm 47 91 105
    • (2000) Dyes Pigm , vol.47 , pp. 91-105
    • Poteau, X.1    Brown, A.2    Brown, R.3    Holmes, C.4    Matthew, D.5
  • 34
    • 1942500245 scopus 로고    scopus 로고
    • + in neutral aqueous solution: 4,5-diaminoalkeneamino-N-alkyl-l,8- naphthalimides
    • + in neutral aqueous solution: 4,5-diaminoalkeneamino-N-alkyl-l,8-naphthalimides Tetrahedron Lett 45 3969 3973
    • (2004) Tetrahedron Lett , vol.45 , pp. 3969-3973
    • Jia, L.1    Zhang, Y.2    Guo, X.3    Qian, X.4
  • 35
    • 0037462272 scopus 로고    scopus 로고
    • A novel family of twisted molecular luminescent materials containing carbazole unit for single-layer organic electroluminescent devices
    • W Zhu M Hu R Yao H Tian 2003 A novel family of twisted molecular luminescent materials containing carbazole unit for single-layer organic electroluminescent devices J Photochem Photobiol A Chem 154 169 177
    • (2003) J Photochem Photobiol A Chem , vol.154 , pp. 169-177
    • Zhu, W.1    Hu, M.2    Yao, R.3    Tian, H.4
  • 37
    • 0042762941 scopus 로고    scopus 로고
    • Fluorescent chromophores functionalized single-wall carbon nanotubes with minimal alteration to their characteristic one-dimensional electronic states
    • W Zhu N Minami S Kazaoui Y Kim 2003 Fluorescent chromophores functionalized single-wall carbon nanotubes with minimal alteration to their characteristic one-dimensional electronic states J Mater Chem 13 2196 2201
    • (2003) J Mater Chem , vol.13 , pp. 2196-2201
    • Zhu, W.1    Minami, N.2    Kazaoui, S.3    Kim, Y.4
  • 38
    • 0141572424 scopus 로고    scopus 로고
    • Synthesis and functional properties of green fluorescent poly(methylmethacrylate) for use in liquid crystal systems
    • I Grabchev JM Chovelon 2003 Synthesis and functional properties of green fluorescent poly(methylmethacrylate) for use in liquid crystal systems Polym Adv Technol 14 601 608
    • (2003) Polym Adv Technol , vol.14 , pp. 601-608
    • Grabchev, I.1    Chovelon, J.M.2
  • 39
    • 0034075703 scopus 로고    scopus 로고
    • Synthesis and properties of fluorescent 1,8-naphthalimide dyes for application in liquid crystal displays
    • I Grabchev I Moneva V Bojinov S Guittonneau 2000 Synthesis and properties of fluorescent 1,8-naphthalimide dyes for application in liquid crystal displays J Mater Chem 10 1291 1296
    • (2000) J Mater Chem , vol.10 , pp. 1291-1296
    • Grabchev, I.1    Moneva, I.2    Bojinov, V.3    Guittonneau, S.4
  • 40
    • 0032580424 scopus 로고    scopus 로고
    • A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide
    • F Cosnard V Wintgens 1998 A new fluoroionophore derived from 4-amino-N-methyl-1,8-naphthalimide Tetrahedron Lett 39 2751 2754
    • (1998) Tetrahedron Lett , vol.39 , pp. 2751-2754
    • Cosnard, F.1    Wintgens, V.2
  • 41
    • 34748915423 scopus 로고    scopus 로고
    • New green fluorescent polymer sensors for metal cations and protons
    • I Grabchev S Sali R Betcheva V Gregoriou 2007 New green fluorescent polymer sensors for metal cations and protons Eur Polym J 43 4297 4305
    • (2007) Eur Polym J , vol.43 , pp. 4297-4305
    • Grabchev, I.1    Sali, S.2    Betcheva, R.3    Gregoriou, V.4
  • 42
    • 0016484758 scopus 로고
    • New coumarin dyes with rigidized structure for flashlamp-pumped dye lasers
    • G Reynolds K Drexhage 1975 New coumarin dyes with rigidized structure for flashlamp-pumped dye lasers Opt Commun 13 222 225
    • (1975) Opt Commun , vol.13 , pp. 222-225
    • Reynolds, G.1    Drexhage, K.2
  • 43
    • 0009587780 scopus 로고
    • A molecular photoionic and gate based on fluorescent signaling
    • A de Silva H Gunaratne C McCoy 1993 A molecular photoionic AND gate based on fluorescent signaling Nature 364 42 44
    • (1993) Nature , vol.364 , pp. 42-44
    • De Silva, A.1    Gunaratne, H.2    McCoy, C.3
  • 44
    • 33748233971 scopus 로고
    • New fluorescent model compounds for the study of photoinduced electron transfer: The influence of molecular electric field in the excited state
    • A de Sivla H Gunaratne JL Habib-Jiwan C McCoy T Rice JP Soumillion 1995 New fluorescent model compounds for the study of photoinduced electron transfer: the influence of molecular electric field in the excited state Angew Chem Int Ed Engl 34 1728 1731
    • (1995) Angew Chem Int Ed Engl , vol.34 , pp. 1728-1731
    • De Sivla, A.1    Gunaratne, H.2    Habib-Jiwan, J.L.3    McCoy, C.4    Rice, T.5    Soumillion, J.P.6
  • 45
    • 0035860111 scopus 로고    scopus 로고
    • Flipping the light switch 'ON'-the design of sensor molecules that show cation-induced fluorescence enhancement with heavy and transition metal ions
    • K Rurack 2001 Flipping the light switch 'ON'-the design of sensor molecules that show cation-induced fluorescence enhancement with heavy and transition metal ions Spectrochim Acta Part A Mol Biomol Spectrosc 57 2161 2195
    • (2001) Spectrochim Acta Part A Mol Biomol Spectrosc , vol.57 , pp. 2161-2195
    • Rurack, K.1
  • 47
    • 0035472769 scopus 로고    scopus 로고
    • Synthesis and photophysical properties of polymerizable 1,8-naphthalimide dyes and their copolymers with styrene
    • I Grabchev V Bojinov H Petkov 2001 Synthesis and photophysical properties of polymerizable 1,8-naphthalimide dyes and their copolymers with styrene Dyes Pigm 51 1 8
    • (2001) Dyes Pigm , vol.51 , pp. 1-8
    • Grabchev, I.1    Bojinov, V.2    Petkov, H.3
  • 48
    • 0036568235 scopus 로고    scopus 로고
    • Photostability of novel copolymers functionalized with laser dyes based on modified rhodamine 6G and 1,8-naphthalimide
    • S Yang F Meng H Tian K Chen 2002 Photostability of novel copolymers functionalized with laser dyes based on modified rhodamine 6G and 1,8-naphthalimide Eur Polym J 38 911 919
    • (2002) Eur Polym J , vol.38 , pp. 911-919
    • Yang, S.1    Meng, F.2    Tian, H.3    Chen, K.4
  • 50
    • 3242665110 scopus 로고    scopus 로고
    • Towards the development of controllable and reversible 'on-off' luminescence switching in soft-matter; Synthesis and spectroscopic investigation of 1,8-naphthalimide-based PET (photoinduced electron transfer) chemosensors for pH in water-permeable hydrogels
    • T Gunnlaugsson C McCoy R Morrow C Phelan F Stomeo 2003 Towards the development of controllable and reversible 'on-off' luminescence switching in soft-matter; synthesis and spectroscopic investigation of 1,8-naphthalimide- based PET (photoinduced electron transfer) chemosensors for pH in water-permeable hydrogels Arkivoc 7 216 228
    • (2003) Arkivoc , vol.7 , pp. 216-228
    • Gunnlaugsson, T.1    McCoy, C.2    Morrow, R.3    Phelan, C.4    Stomeo, F.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.