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Volumn 59, Issue 26, 2003, Pages 4843-4850

Donor-acceptor-donor triads incorporating tetrathiafulvalene and perylene diimide units: Synthesis, electrochemical and spectroscopic studies

Author keywords

Donor acceptor systems; Perylene diimide; Photoinduced electron transfer; Tetrathiafulvalene

Indexed keywords

CHEMICAL COMPOUND; IMIDE; PERYLENE; TETRATHIAFULVALENE DERIVATIVE;

EID: 0038176318     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00700-2     Document Type: Article
Times cited : (73)

References (30)
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    • and references therein
    • Bryce M.R. Adv. Mater. 11:1999;11-23. and references therein.
    • (1999) Adv. Mater. , vol.11 , pp. 11-23
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    • (a) Perepichka D.F., Bryce M.R., Mclnnes E.J.L., Zhao J.P. Org. Lett. 3:2001;1431-1434 (b) Perepichka D.F., Bryce M.R., Batsanov A.S., McInnes E.J.L., Zhao J.P., Farley R.D. Chem. Eur. J. 8:2002;4656-4669.
    • (2001) Org. Lett. , vol.3 , pp. 1431-1434
    • Perepichka, D.F.1    Bryce, M.R.2    Mclnnes, E.J.L.3    Zhao, J.P.4
  • 18
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    • On one hand, these groups will improve their solubility in organic solvents. On the other hand, the steric hindrance of these groups will affect their tendency to aggregate, possibly due to π-π interactions. This is due to fact that both neutral TTF and PI units as well as their radical ions after oxidation or after reduction tend to aggregate in solution
    • On one hand, these groups will improve their solubility in organic solvents. On the other hand, the steric hindrance of these groups will affect their tendency to aggregate, possibly due to π-π interactions. This is due to fact that both neutral TTF and PI units as well as their radical ions after oxidation or after reduction tend to aggregate in solution.
  • 21
    • 85031170303 scopus 로고    scopus 로고
    • Efforts were made to separate the cis/trans isomers, but failed. However, theoretical calculation indicates that these cis/trans isomers show similar electronic structures. Thus, these cis/trans isomers should have no significant difference in their electronic spectra as well as redox potentials. The calculation was performed using the semiempirical AM1 method (Ampec6.7 program)
    • Efforts were made to separate the cis/trans isomers, but failed. However, theoretical calculation indicates that these cis/trans isomers show similar electronic structures. Thus, these cis/trans isomers should have no significant difference in their electronic spectra as well as redox potentials. The calculation was performed using the semiempirical AM1 method (Ampec6.7 program).
  • 22
    • 85031169683 scopus 로고    scopus 로고
    • The spectra were measured at low concentrations in order to study the intrinsic intramolecular charge-transfer interaction for triads 1-3
    • The spectra were measured at low concentrations in order to study the intrinsic intramolecular charge-transfer interaction for triads 1-3.
  • 23
    • 85031164873 scopus 로고    scopus 로고
    • The fact that intramolecular charge-transfer interactions in triads 1-3 are negligible is unexpected, in particular for triad 1, for which a rather long and flexible spacer is employed. Structural optimization, using the standard procedure for energy minimization with Ampec6.7 program, indicates that the most stable conformations for triads 1-3 are extended ones, even in the case of triad 1 . Consequently, we preliminarily ascribe this experimental finding to the difference in spatial separation of electron donor and acceptor units for these triads. The spatial distances between TTF and PI units were estimated by semiempirical AM1 method with Ampec6.7 program as follows: 25 Å for 1 ; 12 Å for 2 ; 12 Å for 3 . For this estimation, we assume the 'cyclohexane' spacers in triads 2 and 3 are in the chair conformation
    • The fact that intramolecular charge-transfer interactions in triads 1-3 are negligible is unexpected, in particular for triad 1, for which a rather long and flexible spacer is employed. Structural optimization, using the standard procedure for energy minimization with Ampec6.7 program, indicates that the most stable conformations for triads 1-3 are extended ones, even in the case of triad 1 . Consequently, we preliminarily ascribe this experimental finding to the difference in spatial separation of electron donor and acceptor units for these triads. The spatial distances between TTF and PI units were estimated by semiempirical AM1 method with Ampec6.7 program as follows: 25 Å for 1 ; 12 Å for 2 ; 12 Å for 3 . For this estimation, we assume the 'cyclohexane' spacers in triads 2 and 3 are in the chair conformation.
  • 24
    • 84991138979 scopus 로고
    • * proceeds readily and results in fluorescence quenching. ΔG values (kJ/mol) were obtained for triad
    • * proceeds readily and results in fluorescence quenching. ΔG values (kJ/mol) were obtained for triad 1 (-113.8), triad 2 (-114.8) and triad 3 (-113.8) respectively estimated by the Rehm-Weller equation according to the reference Rehm D., Weller D. Isr. J. Chem. 8:1970;259-271.
    • (1970) Isr. J. Chem. , vol.8 , pp. 259-271
    • Rehm, D.1    Weller, D.2
  • 25
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    • Here, we mean the energy 'donor' is PI unit, while the energy 'acceptor' is TTF unit
    • Here, we mean the energy 'donor' is PI unit, while the energy 'acceptor' is TTF unit.
  • 28
    • 85031175920 scopus 로고    scopus 로고
    • The dark-colored precipitate showed the molecular ion peak at m/z=1658.5 in MS spectrum (measured by MALDI-TOF) which was the same as that of triad 1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.