메뉴 건너뛰기




Volumn 112, Issue 37, 2008, Pages 14626-14638

Ground- and excited-state pinched cone equilibria in calix[4]arenes bearing two perylene bisimide dyes

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRON TRANSITIONS;

EID: 53149103564     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp804068b     Document Type: Article
Times cited : (81)

References (117)
  • 1
    • 0004287470 scopus 로고    scopus 로고
    • Asfari, Z, Böhmer, V, Harrowfield, J, Eds, Kluwer Academic Publishers: Dordrecht
    • (a) Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001.
    • (2001) Calixarenes 2001
  • 2
    • 0004146786 scopus 로고
    • Gutsche, C. D, Ed, The Royal Society of Chemistry: Cambridge, U.K
    • (b) Calixarenes; Gutsche, C. D., Ed.; The Royal Society of Chemistry: Cambridge, U.K., 1993.
    • (1993) Calixarenes
  • 3
    • 0004268367 scopus 로고    scopus 로고
    • Gutsche, C. D, Ed, The Royal Society of Chemistry: Letchworth, U.K
    • (c) Calixarenes Revisited; Gutsche, C. D., Ed.; The Royal Society of Chemistry: Letchworth, U.K., 1998.
    • (1998) Calixarenes Revisited
  • 5
    • 0004266535 scopus 로고    scopus 로고
    • Mandolini, L, Ungaro, R, Eds, Imperial College Press: London
    • (e) Calixarenes in Action; Mandolini, L., Ungaro, R., Eds.; Imperial College Press: London, 2000.
    • (2000) Calixarenes in Action
  • 29
    • 84989571860 scopus 로고    scopus 로고
    • Timmerman, P.; Nierop, K. G. A.; Brinks, E. A.; Verboom, W.; van Veggel, F. C.; J, M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. - Eur. J. 1995, 1, 132-143.
    • (c) Timmerman, P.; Nierop, K. G. A.; Brinks, E. A.; Verboom, W.; van Veggel, F. C.; J, M.; van Hoorn, W. P.; Reinhoudt, D. N. Chem. - Eur. J. 1995, 1, 132-143.
  • 33
    • 53149117690 scopus 로고    scopus 로고
    • Supramolecular Dye Chemistry; Würthner, F., Ed.; Topics in Current Chemistry 258, Springer-Verlag: Berlin, 2005.
    • (b) Supramolecular Dye Chemistry; Würthner, F., Ed.; Topics in Current Chemistry 258, Springer-Verlag: Berlin, 2005.
  • 55
    • 53149154120 scopus 로고    scopus 로고
    • Seybold, G.; Stange, A. (BASF AG), Ger. Pat. DE 35 45 004, 1987 (Chem. Abstr. 1988, 108, 77134c).
    • Seybold, G.; Stange, A. (BASF AG), Ger. Pat. DE 35 45 004, 1987 (Chem. Abstr. 1988, 108, 77134c).
  • 58
    • 0037167048 scopus 로고    scopus 로고
    • For examples with rigid spacer units containing PBIs, see a
    • For examples with rigid spacer units containing PBIs, see (a) Giaimo, J. M.; Gusev, A. V.; Wasielewski, M. R J. Am. Chem. Soc. 2002, 124, 8530-8531.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 8530-8531
    • Giaimo, J.M.1    Gusev, A.V.2    Wasielewski, M.R.3
  • 63
    • 0037182680 scopus 로고    scopus 로고
    • For other bis-chromophoric systems, see a
    • For other bis-chromophoric systems, see (a) Jokic, D.; Asfari, Z.; Weiss, J. Org. Lett. 2002, 4, 2129-2132.
    • (2002) Org. Lett , vol.4 , pp. 2129-2132
    • Jokic, D.1    Asfari, Z.2    Weiss, J.3
  • 81
    • 53149108067 scopus 로고    scopus 로고
    • 4.
    • 4.
  • 86
    • 4444276207 scopus 로고    scopus 로고
    • For examples containing PBI dyes, see refs 21, 23f, and (a) Li, X.; Sinks, L. E.; Rybtchinski, B.; Wasielewski, M. R J. Am. Chem. Soc. 2004, 126, 10810-10811.
    • For examples containing PBI dyes, see refs 21, 23f, and (a) Li, X.; Sinks, L. E.; Rybtchinski, B.; Wasielewski, M. R J. Am. Chem. Soc. 2004, 126, 10810-10811.
  • 91
    • 53149154339 scopus 로고    scopus 로고
    • 4 was chosen as a solvent because precipitation of compounds o2c and g2c is observed after approximately 30 min for the solution of both o2c and g2c in MCH, respectively.
    • 4 was chosen as a solvent because precipitation of compounds o2c and g2c is observed after approximately 30 min for the solution of both o2c and g2c in MCH, respectively.
  • 92
    • 53149086501 scopus 로고    scopus 로고
    • Notably, all UV/vis absorption spectra show a small blue shift with increasing temperature, and a slightly reduced peak intensity for the absorption maximum. These spectral changes are observed for both the monomelic and dimeric series as well as for the respective reference compounds without calix[4]arene substitution see Figures S12 and S13 in the Supporting Information, Hence, the observed effects appear to be independent of the respective PBI unit as well as the calix[4]arene substitution on the chromophore. We attribute the hypsochromic shift to a decrease of the dielectric constant of CCl4 with increasing temperature,35 and the reduced absorption coefficient is attributed to the broadening of the absorption band due to the population of more conformations at higher temperature
    • 35 and the reduced absorption coefficient is attributed to the broadening of the absorption band due to the population of more conformations at higher temperature.
  • 93
    • 53149148735 scopus 로고    scopus 로고
    • This is supported by the fact that, for compound oref, a hypsochromic shift of the band maximum from 523 nm in CCl4 (with a relative permittivity of ε@293 K, 2.24) to 517 nm (ε@293 K, 2.02) in MCH is observed. Hence, lowering the solvent polarity of Δε ≈ 0.2 leads to a spectral shift of about 6 nm. For the permittivity of CCl 4 at 343 K, a value of ε, 2.14 is given, and, accordingly, an increase of temperature between 293 and 343 K leads to a reduced permittivity of Δε ≈ 0.1, resulting in a hypsochromic shift of the band maximum of 3 nm from 523 nm (T, 293 K) to 520 nm (T, 343 K, Similar behavior is also found for compound gref (with 17 nm shift upon solvent change with Δε RS 0.2, and with 8 nm shift upon temperature change with Δε ≈ 0.1) and compound rref with 11 nm shift upon solvent change with Δε ≈ 0.2, and with 5 nm shift upon temperatur
    • 4 at 343 K, a value of ε = 2.14 is given, and, accordingly, an increase of temperature between 293 and 343 K leads to a reduced permittivity of Δε ≈ 0.1, resulting in a hypsochromic shift of the band maximum of 3 nm from 523 nm (T = 293 K) to 520 nm (T = 343 K). Similar behavior is also found for compound gref (with 17 nm shift upon solvent change with Δε RS 0.2, and with 8 nm shift upon temperature change with Δε ≈ 0.1) and compound rref (with 11 nm shift upon solvent change with Δε ≈ 0.2, and with 5 nm shift upon temperature change with Δε ≈ 0.1). For temperature-dependent permittivity values, see CRC Handbook of Chemistry and Physics, 76th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1995.
  • 94
    • 53149148346 scopus 로고    scopus 로고
    • 24c In contrast, the orange reference compound oref reveals quantum yields of almost unity in all five solvents (see Table 1).
    • 24c In contrast, the orange reference compound oref reveals quantum yields of almost unity in all five solvents (see Table 1).
  • 96
    • 0029633186 scopus 로고    scopus 로고
    • Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheatham, T. E., 10; De Bolt, S.; Ferguson, D.; Seibel, G.; Kollman, P. Comput. Phys. Commun. 1995, 91, 1-41.
    • (b) Pearlman, D. A.; Case, D. A.; Caldwell, J. W.; Ross, W. S.; Cheatham, T. E., 10; De Bolt, S.; Ferguson, D.; Seibel, G.; Kollman, P. Comput. Phys. Commun. 1995, 91, 1-41.
  • 102
    • 0035969569 scopus 로고    scopus 로고
    • Longer-lived excited states due to PBI-excimer formation have been reported in the literature; see (a) Katoh, R, Sinha, S, Murata, S, Tachiya, M. J. Photochem. Photobiol, A 2001, 145, 23-34
    • Longer-lived excited states due to PBI-excimer formation have been reported in the literature; see (a) Katoh, R.; Sinha, S.; Murata, S.; Tachiya, M. J. Photochem. Photobiol., A 2001, 145, 23-34.
  • 105
    • 53149112161 scopus 로고    scopus 로고
    • For all lifetimes determined for compounds g2c, gc, and gref, biexponential decays are observed. Accordingly, additional small components of ca. 0.5 ns are found for each compound independent of the solvent polarity and of the calix[4]arene substitution of the chromophore. The latter components are thus considered to be independent of the calix[4]arene substitution of the dye unit and are inherent to the green PBI chromophore itself (for details refer to Table 3).
    • For all lifetimes determined for compounds g2c, gc, and gref, biexponential decays are observed. Accordingly, additional small components of ca. 0.5 ns are found for each compound independent of the solvent polarity and of the calix[4]arene substitution of the chromophore. The latter components are thus considered to be independent of the calix[4]arene substitution of the dye unit and are inherent to the green PBI chromophore itself (for details refer to Table 3).
  • 107
    • 53149092307 scopus 로고    scopus 로고
    • Solutions of o2c and oc in the lowest polarity solvent MCH could not be measured due to precipitation of the compounds.
    • Solutions of o2c and oc in the lowest polarity solvent MCH could not be measured due to precipitation of the compounds.
  • 113
    • 53149104218 scopus 로고    scopus 로고
    • Global and target analysis can be performed with, e.g, the R package TIMP; see
    • (d) Global and target analysis can be performed with, e.g., the R package TIMP; see http://cran.r-project.org/doc/packages/TIMP.pdf.
  • 116
    • 53149087298 scopus 로고    scopus 로고
    • An excited-state charge transfer process resulting in a charge transfer state of the jr-stacked form could not be unambiguously confirmed by global and target analysis
    • An excited-state charge transfer process resulting in a charge transfer state of the jr-stacked form could not be unambiguously confirmed by global and target analysis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.