메뉴 건너뛰기




Volumn 2, Issue 3, 2003, Pages 342-353

Singlet excited state dipole moments of dual fluorescent N-phenylpyrroles and 4-(dimethylamino)benzonitrile from solvatochromic and thermochromic spectral shifts

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLPYRROLE; 4 (DIMETHYLAMINO)BENZONITRILE; AMINOBENZONITRILE; BENZENE DERIVATIVE; BENZONITRILE; CYANIDE; ETHER; N (3 CYANOPHENYL)PYROLE; N (4 CYANOPHENYL)PYRROLE; N (4 METHYLPHENYL)PYRROLE; N PROPYL CYANIDE; NITRILE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0344810166     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b211838f     Document Type: Article
Times cited : (77)

References (46)
  • 1
    • 0000075514 scopus 로고
    • Population of excited charge transfer states and molecular conformation in N-phenylpyrroles
    • W. Rettig and F. Marschner, Population of excited charge transfer states and molecular conformation in N-phenylpyrroles, Nouv. J. Chim., 1983, 7, 425-431.
    • (1983) Nouv. J. Chim. , vol.7 , pp. 425-431
    • Rettig, W.1    Marschner, F.2
  • 2
    • 84985609328 scopus 로고
    • Charge separation in excited states of decoupled systems-TICT compounds and implications regarding the development of new laser dyes and the primary processes of vision and photosynthesis
    • W. Rettig, Charge separation in excited states of decoupled systems-TICT compounds and implications regarding the development of new laser dyes and the primary processes of vision and photosynthesis, Angew. Chem., Int. Ed. Engl., 1986, 25, 971-988.
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 971-988
    • Rettig, W.1
  • 3
    • 0001310139 scopus 로고
    • Molecular conformation and biradicaloid charge transfer states in substituted N-phenylpyrroles
    • W. Rettig and F. Marschner, Molecular conformation and biradicaloid charge transfer states in substituted N-phenylpyrroles, New. J. Chem., 1990, 14, 819-824.
    • (1990) New. J. Chem. , vol.14 , pp. 819-824
    • Rettig, W.1    Marschner, F.2
  • 4
    • 27844449915 scopus 로고    scopus 로고
    • See the remark on the meaning of LE in ref. 5.
    • See the remark on the meaning of LE in ref. 5.
  • 5
    • 0037019458 scopus 로고    scopus 로고
    • Picosecond and nanosecond fluorescence decays of 4-(dimethylamino)- phenylacetylene in comparison with those of 4-(dimethylamino)-benzonitrile. No evidence for intramolecular charge transfer and a nonfluorescing intramolecular charge transfer state
    • K. A. Zachariasse, T. Yoshihara and S. I. Druzhinin, Picosecond and nanosecond fluorescence decays of 4-(dimethylamino)-phenylacetylene in comparison with those of 4-(dimethylamino)-benzonitrile. No evidence for intramolecular charge transfer and a nonfluorescing intramolecular charge transfer state, J. Phys. Chem. A, 2002, 106, 6325-6333;
    • (2002) J. Phys. Chem. A , vol.106 , pp. 6325-6333
    • Zachariasse, K.A.1    Yoshihara, T.2    Druzhinin, S.I.3
  • 6
    • 79959372541 scopus 로고    scopus 로고
    • See correction
    • See correction in J. Phys. Chem. A, 2002, 106, 8978.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 8978
  • 7
    • 0001553843 scopus 로고
    • A study on the spectroscopy and photophysics of N-phenyl pyrrole and N-phenyl pyrazole
    • A. Sarkar and S. Chakravorti, A study on the spectroscopy and photophysics of N-phenyl pyrrole and N-phenyl pyrazole, Chem. Phys. Lett., 1995, 235, 195-201.
    • (1995) Chem. Phys. Lett. , vol.235 , pp. 195-201
    • Sarkar, A.1    Chakravorti, S.2
  • 8
    • 0036247291 scopus 로고    scopus 로고
    • Time-resolved dual fluorescence of 1-phenylpyrrole in acetonitrile: Molecular dynamics simulations of solvent response to twisted intramolecular charge transfer
    • J. Manz, B. Proppe and B. Schmidt, Time-resolved dual fluorescence of 1-phenylpyrrole in acetonitrile: molecular dynamics simulations of solvent response to twisted intramolecular charge transfer, Phys. Chem. Chem. Phys., 2002, 4, 1876-1881.
    • (2002) Phys. Chem. Chem. Phys. , vol.4 , pp. 1876-1881
    • Manz, J.1    Proppe, B.2    Schmidt, B.3
  • 9
    • 0001036696 scopus 로고    scopus 로고
    • Dual fluorescence and multiple charge transfer nature in derivatives of N-pyrrolobenzonitrile
    • C. Cornelissen-Gude and W. Rettig, Dual fluorescence and multiple charge transfer nature in derivatives of N-pyrrolobenzonitrile, J. Phys. Chem. A, 1998, 102, 7754-7760.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 7754-7760
    • Cornelissen-Gude, C.1    Rettig, W.2
  • 10
    • 11644298376 scopus 로고
    • Application of a simplified microstructural solvent interaction model to the solvatochromism of twisted intramolecular charge transfer
    • W. Rettig, Application of a simplified microstructural solvent interaction model to the solvatochromism of twisted intramolecular charge transfer, J. Mol. Struct., 1982, 84, 303-327.
    • (1982) J. Mol. Struct. , vol.84 , pp. 303-327
    • Rettig, W.1
  • 11
    • 27844513809 scopus 로고    scopus 로고
    • note
    • e(ICT) = 22.4 D. The ICT dipole moment of PP4C was found in ref. 9 to be larger than that of DMABN (12.2 D with ρ = 5.00 Å).
  • 13
    • 0001511832 scopus 로고    scopus 로고
    • Electronic spectra of jet-cooled I-phenylpyrrole: Large amplitude torsional motion and twisted intramolecular charge-transfer phenomena
    • K. Okuyama, Y. Numata, S. Odawara and I. Suzuka, Electronic spectra of jet-cooled I-phenylpyrrole: large amplitude torsional motion and twisted intramolecular charge-transfer phenomena, J. Chem. Phys., 1998, 109, 7185-7195.
    • (1998) J. Chem. Phys. , vol.109 , pp. 7185-7195
    • Okuyama, K.1    Numata, Y.2    Odawara, S.3    Suzuka, I.4
  • 14
    • 0037163528 scopus 로고    scopus 로고
    • Jet cooled spectra of pyrrolobenzene and of pyrrolobenzonitrile: The nature of the excited states
    • L. Belau, Y. Haas and W. Rettig, Jet cooled spectra of pyrrolobenzene and of pyrrolobenzonitrile: the nature of the excited states, Chem. Phys. Lett., 2002, 364, 157-163.
    • (2002) Chem. Phys. Lett. , vol.364 , pp. 157-163
    • Belau, L.1    Haas, Y.2    Rettig, W.3
  • 15
    • 0037061995 scopus 로고    scopus 로고
    • Picosecond infrared spectrum of 4-(pyrrol-1-yl)benzonitrile: Structure of the excited charge-transfer states of donor-acceptor systems
    • H. Okamoto and M. Kinoshita, Picosecond infrared spectrum of 4-(pyrrol-1-yl)benzonitrile: structure of the excited charge-transfer states of donor-acceptor systems, J. Phys. Chem. A, 2002, 106, 3485-3490.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 3485-3490
    • Okamoto, H.1    Kinoshita, M.2
  • 17
    • 0001449956 scopus 로고    scopus 로고
    • Theoretical study of the twisted intramolecular charge transfer in 1-phenylpyrrole
    • B. Proppe, M. Merchán and L. Serrano-Andrés, Theoretical study of the twisted intramolecular charge transfer in 1-phenylpyrrole, J. Phys. Chem. A, 2000, 104, 1608-1616.
    • (2000) J. Phys. Chem. A , vol.104 , pp. 1608-1616
    • Proppe, B.1    Merchán, M.2    Serrano-Andrés, L.3
  • 18
    • 0034671312 scopus 로고    scopus 로고
    • A DFT/MRCI study on the excited state charge transfer states of N-pyrrolobenzene, N-pyrrolobenzonitrile and 4-N,N-dimelhylaminobenzonitrile
    • A. B. J. Parusel, A DFT/MRCI study on the excited state charge transfer states of N-pyrrolobenzene, N-pyrrolobenzonitrile and 4-N,N- dimelhylaminobenzonitrile, Phys. Chem. Chem. Phys., 2000, 2, 5545-5552.
    • (2000) Phys. Chem. Chem. Phys. , vol.2 , pp. 5545-5552
    • Parusel, A.B.J.1
  • 19
    • 27844493228 scopus 로고    scopus 로고
    • note
    • The equation employed in ref. 17 to estimate the solvent stabilisation is different from that used here, cf. eqns. (1)-(4).
  • 20
    • 0037050570 scopus 로고    scopus 로고
    • The nature of the intramolecular charge transfer excited state in p-pyrrolocyanobenzene (PBN) and other derivatives of benzene substituted by electron donor and acceptor groups
    • S. Zilberg and Y. Haas, The nature of the intramolecular charge transfer excited state in p-pyrrolocyanobenzene (PBN) and other derivatives of benzene substituted by electron donor and acceptor groups, J. Phys. Chem. A, 2002, 106, 1-11.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 1-11
    • Zilberg, S.1    Haas, Y.2
  • 22
    • 0002602510 scopus 로고    scopus 로고
    • The PICT model for dual fluorescence of aminobenzonitriles
    • K. A. Zachariasse, The PICT model for dual fluorescence of aminobenzonitriles, Chem. Phys. Lett., 2000, 320, 8-13.
    • (2000) Chem. Phys. Lett. , vol.320 , pp. 8-13
    • Zachariasse, K.A.1
  • 23
    • 0001335830 scopus 로고
    • Twisted intramolecular charge transfer states (TICT). A new class of excited states with a full charge separation
    • Z. R. Grabowski, K. Rotkiewicsz, A. Siemiarczuk, D. J. Cowley and W. Baumann, Twisted intramolecular charge transfer states (TICT). A new class of excited states with a full charge separation, Nouv. J. Chim., 1979, 3, 443-454.
    • (1979) Nouv. J. Chim. , vol.3 , pp. 443-454
    • Grabowski, Z.R.1    Rotkiewicsz, K.2    Siemiarczuk, A.3    Cowley, D.J.4    Baumann, W.5
  • 25
    • 0031559454 scopus 로고    scopus 로고
    • Absence of dual fluorescence with 4-(dimethylamino)phenylacetylene. A comparison between experimental results and theoretical predictions
    • K. A. Zachariasse, M. Grobys and E. Tauer, Absence of dual fluorescence with 4-(dimethylamino)phenylacetylene. A comparison between experimental results and theoretical predictions, Chem. Phys. Lett., 1997, 274, 372-382.
    • (1997) Chem. Phys. Lett. , vol.274 , pp. 372-382
    • Zachariasse, K.A.1    Grobys, M.2    Tauer, E.3
  • 26
    • 0001407795 scopus 로고
    • Excited-state dipole moments of dual fluorescent 4-(dialkylamino) benzonitriles. Influence of alkyl chain length and effective solvent polarity
    • W. Schuddeboom, S. A. Jonker, J. M. Warman, U. Leinhos, W. Kühnle and K. A. Zachariasse, Excited-state dipole moments of dual fluorescent 4-(dialkylamino)benzonitriles. Influence of alkyl chain length and effective solvent polarity, J. Phys. Chem., 1992, 96, 10809-10819.
    • (1992) J. Phys. Chem. , vol.96 , pp. 10809-10819
    • Schuddeboom, W.1    Jonker, S.A.2    Warman, J.M.3    Leinhos, U.4    Kühnle, W.5    Zachariasse, K.A.6
  • 27
    • 0039120671 scopus 로고    scopus 로고
    • Photophysics of 4-dimethylamino-4′-cyanostilbene and 4-azetidinyl-4′-cyanostilbene. Time-resolved fluorescence and trans-cis photoisomerisation
    • Yu. V. Il'ichev, W. Kühnle and K. A. Zachariasse, Photophysics of 4-dimethylamino-4′-cyanostilbene and 4-azetidinyl-4′-cyanostilbene. Time-resolved fluorescence and trans-cis photoisomerisation, Chem. Phys., 1996, 211, 441-453.
    • (1996) Chem. Phys. , vol.211 , pp. 441-453
    • Il'Ichev, Y.V.1    Kühnle, W.2    Zachariasse, K.A.3
  • 28
    • 0001269334 scopus 로고
    • Dipole moments and polarizabilities of molecules in excited electronic states
    • ed. E. C. Lim, Academic Press, New York
    • W. Liptay, Dipole moments and polarizabilities of molecules in excited electronic states, in Excited States, vol. 1, ed. E. C. Lim, Academic Press, New York, 1974, p. 129.
    • (1974) Excited States , vol.1 , pp. 129
    • Liptay, W.1
  • 30
    • 0001016232 scopus 로고
    • Structure and crystal packing of 4-amino-benzonitriles and 4-amino-3,5-dimethylbenzonitriles at various temperatures
    • A. Heine, R. Herbst-Irmer, D. Stalke, W. Kühnle and K. A. Zachariasse, Structure and crystal packing of 4-amino-benzonitriles and 4-amino-3,5-dimethylbenzonitriles at various temperatures, Acta Crystallogr., Sect. B, 1994, 50, 363-371.
    • (1994) Acta Crystallogr., Sect. B , vol.50 , pp. 363-371
    • Heine, A.1    Herbst-Irmer, R.2    Stalke, D.3    Kühnle, W.4    Zachariasse, K.A.5
  • 32
    • 0001622866 scopus 로고    scopus 로고
    • Dual fluorescence and fast intramolecular charge transfer with 4-(diisopropylamino)benzonitrile in alkane solvents
    • A. Demeter, S. Druzhinin, M. George, E. Haselbach, J.-L. Roulin and K. A. Zachariasse, Dual fluorescence and fast intramolecular charge transfer with 4-(diisopropylamino)benzonitrile in alkane solvents, Chem. Phys. Lett., 2000, 323, 351-360.
    • (2000) Chem. Phys. Lett. , vol.323 , pp. 351-360
    • Demeter, A.1    Druzhinin, S.2    George, M.3    Haselbach, E.4    Roulin, J.-L.5    Zachariasse, K.A.6
  • 33
    • 0004177513 scopus 로고    scopus 로고
    • The Royal Society of Chemistry, Cambridge, UK, ch. 9.
    • P. Suppan N. Ghoneim, Solvatochromism, The Royal Society of Chemistry, Cambridge, UK, 1997, ch. 9.
    • (1997) Solvatochromism
    • Suppan, P.1    Ghoneim, N.2
  • 34
    • 0000417558 scopus 로고
    • Characteristics of molecular complexes in the excited state
    • H. Beens and A. Weller, Characteristics of molecular complexes in the excited state, Acta Phys. Pol., 1968, 34, 593-542.
    • (1968) Acta Phys. Pol. , vol.34 , pp. 593-1542
    • Beens, H.1    Weller, A.2
  • 35
    • 0000247404 scopus 로고
    • A dipole moment study of gradually hindered N-phenylpyrroles
    • H. Lumbroso, D. M. Bertin and F. Marschner, A dipole moment study of gradually hindered N-phenylpyrroles, J. Mol. Struct., 1988, 178, 187-200.
    • (1988) J. Mol. Struct. , vol.178 , pp. 187-200
    • Lumbroso, H.1    Bertin, D.M.2    Marschner, F.3
  • 37
    • 0000018296 scopus 로고
    • Temperature effects in solvatochromic shifts
    • P. Suppan, Temperature effects in solvatochromic shifts, J. Chem. Soc., Faraday Trans. 2, 1981, 77, 1553-1562.
    • (1981) J. Chem. Soc., Faraday Trans. 2 , vol.77 , pp. 1553-1562
    • Suppan, P.1
  • 38
    • 0022028640 scopus 로고
    • Thermochromic shifts of the fluorescence spectra of 4-N,N- dimethylaminobenzonitrile in solution
    • P. Suppan, Thermochromic shifts of the fluorescence spectra of 4-N,N-dimethylaminobenzonitrile in solution, J. Lumin., 1985, 33, 29-32.
    • (1985) J. Lumin. , vol.33 , pp. 29-32
    • Suppan, P.1
  • 39
    • 0000372690 scopus 로고
    • Thermochromic shifts of some molecular and exciplex fluorescence spectra
    • T. Hagan, D. Pilloud and P. Suppan, Thermochromic shifts of some molecular and exciplex fluorescence spectra, Chem. Phys. Lett., 1987, 139, 499-502.
    • (1987) Chem. Phys. Lett. , vol.139 , pp. 499-502
    • Hagan, T.1    Pilloud, D.2    Suppan, P.3
  • 40
    • 0347462845 scopus 로고
    • Solvatochromic shifts: The influence of the medium on the energy of electronic states
    • P. Suppan, Solvatochromic shifts: the influence of the medium on the energy of electronic states, J. Photochem. Photobiol. A, 1990, 50, 293-330.
    • (1990) J. Photochem. Photobiol. A , vol.50 , pp. 293-330
    • Suppan, P.1
  • 41
    • 0009966098 scopus 로고
    • Über die Temperaturabhängigkeit der Absorptions- Und Fluoreszenzspektren von 4-Amino-phthalimid
    • A. Kawski and W. Kolakowski, Über die Temperaturabhängigkeit der Absorptions- und Fluoreszenzspektren von 4-Amino-phthalimid, Acta Phys. Pol., 1966, 29, 177-186.
    • (1966) Acta Phys. Pol. , vol.29 , pp. 177-186
    • Kawski, A.1    Kolakowski, W.2
  • 42
    • 84912823528 scopus 로고
    • Temperaturabhängigkeit der statischen Dielektrizitätskonstante und des optischen Brechungsindexes von Flüssigkeiten
    • I. Gryczynski and A. Kawski, Temperaturabhängigkeit der statischen Dielektrizitätskonstante und des optischen Brechungsindexes von Flüssigkeiten, Z. Naturforsch., 1975, 30A, 287-291.
    • (1975) Z. Naturforsch. , vol.30 A , pp. 287-291
    • Gryczynski, I.1    Kawski, A.2
  • 43
    • 0000052059 scopus 로고
    • Molecular conformation and excited-state dipole moments of di- and tetramethylaminobenzonitrile (DMABN and TMABN)
    • W. Rettig, D. Braun, P. Suppan, E. Vauthey, K. Rotkiewicsz, R. Luboradzki and K. Suwińska, Molecular conformation and excited-state dipole moments of di- and tetramethylaminobenzonitrile (DMABN and TMABN), J. Phys. Chem., 1993, 97, 13500-13507.
    • (1993) J. Phys. Chem. , vol.97 , pp. 13500-13507
    • Rettig, W.1    Braun, D.2    Suppan, P.3    Vauthey, E.4    Rotkiewicsz, K.5    Luboradzki, R.6    Suwińska, K.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.