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Volumn 8, Issue 20, 2002, Pages 4656-4669

Engineering a remarkably low HOMO-LUMO gap by covalent linkage of a strong π-donor and a π-acceptor - Tetrathiafulvalene-σ-polynitrofluorene diads: Their amphoteric redox behavior, electron transfer and spectroscopic properties

Author keywords

Donor acceptor systems; Electrochromism; Electron transfer; HOMO LUMO gap; Tetrathiafulvalene

Indexed keywords

CHARGE TRANSFER; CONDENSATION; ELECTRON TRANSITIONS; REDOX REACTIONS; SPECTROSCOPY; STOICHIOMETRY; X RAY CRYSTALLOGRAPHY;

EID: 0037131431     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021018)8:20<4656::AID-CHEM4656>3.0.CO;2-1     Document Type: Article
Times cited : (48)

References (78)
  • 14
    • 0037083756 scopus 로고    scopus 로고
    • d) S. Fuzukumi, K. Okamoto, H. Imahori, Angew Chem. 2002, 114, 642-644; Angew. Chem. Int. Ed. 2002, 41, 620-622.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 620-622
  • 16
    • 0032835693 scopus 로고    scopus 로고
    • b) for recent discussions of this proposal see: R. M. Metzger, J. Mater. Chem. 1999, 9, 2027-2036: R. M. Metzger. J. Mater. Chem. 2000, 10, 55-62.
    • (1999) J. Mater. Chem. , vol.9 , pp. 2027-2036
    • Metzger, R.M.1
  • 17
    • 0034116659 scopus 로고    scopus 로고
    • b) for recent discussions of this proposal see: R. M. Metzger, J. Mater. Chem. 1999, 9, 2027-2036; R. M. Metzger. J. Mater. Chem. 2000, 10, 55-62.
    • (2000) J. Mater. Chem. , vol.10 , pp. 55-62
    • Metzger, R.M.1
  • 18
    • 0033531052 scopus 로고    scopus 로고
    • and references therein
    • a) M. R. Bryce, Adv. Mater. 1999, 11, 11-23 and references therein;
    • (1999) Adv. Mater. , vol.11 , pp. 11-23
    • Bryce, M.R.1
  • 27
    • 0000155467 scopus 로고    scopus 로고
    • j) J. L. Segura, N. Martín. Angew. Chem. 2001, 113, 1416-1455; Angew. Chem. Int. Ed. 2001, 40, 1372-1409.
    • (2001) Angew. Chem. , vol.113 , pp. 1416-1455
    • Segura, J.L.1    Martín, N.2
  • 28
    • 0035901526 scopus 로고    scopus 로고
    • j) J. L. Segura, N. Martín. Angew. Chem. 2001, 113, 1416-1455; Angew. Chem. Int. Ed. 2001, 40, 1372-1409.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1372-1409
  • 36
    • 2142789548 scopus 로고    scopus 로고
    • note
    • Even scratches on the glass or a polished surface of a joint could promote this side reaction, so very smooth glassware or a plastic flask is recommended to minimize the by-product formation. For the same reason, it is difficult to use TLC to monitor the reaction (excessive colorization occurs when the reaction solution is put on a silica gel or alumina TLC plate).
  • 38
    • 2142785705 scopus 로고    scopus 로고
    • note
    • Elemental analysis of the silica gel (LabPro, 40/60 for chromatography) gave K, 0.64%.
  • 40
    • 2142722525 scopus 로고    scopus 로고
    • note
    • Unfortunately, the extremely low intensity of the CN peak in solution precludes a study of the solution IR behavior of this band.
  • 41
    • 2142740700 scopus 로고    scopus 로고
    • note
    • -1, which is due to overlap with the peak from the solvate molecule of MeCN.
  • 43
    • 2142787006 scopus 로고    scopus 로고
    • note
    • The assignment of the protons has been made by comparison with previously investigated fluorene derivatives and on the basis of a COSY experiment (for compound 15).
  • 45
    • 2142727633 scopus 로고    scopus 로고
    • note
    • The same signal was observed for 16.
  • 48
    • 2142735110 scopus 로고    scopus 로고
    • note
    • -3M, indicating that [6·11] CTC is responsible for the EPR signal.
  • 54
    • 33748215599 scopus 로고
    • M. R. Bryce, W. Devonport, A. J. Moore, Angew. Chem. 1994, 106, 1862-1864; Angew. Chem. Int. Ed. 1994, 33, 1761-1763.
    • (1994) Angew. Chem. Int. Ed. , vol.33 , pp. 1761-1763
  • 55
    • 0002879657 scopus 로고    scopus 로고
    • ref. [1a]
    • 0) eV: a) ref. [1a]; b) V. D. Parker, J. Am. Chem. Soc. 1976, 98, 98-103; L. E. Lyons, Aust. J. Chem. 1980, 33, 1717-1725.
  • 56
    • 0002879657 scopus 로고    scopus 로고
    • 0) eV: a) ref. [1a]; b) V. D. Parker, J. Am. Chem. Soc. 1976, 98, 98-103; L. E. Lyons, Aust. J. Chem. 1980, 33, 1717-1725.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 98-103
    • Parker, V.D.1
  • 57
    • 0011135224 scopus 로고
    • 0) eV: a) ref. [1a]; b) V. D. Parker, J. Am. Chem. Soc. 1976, 98, 98-103; L. E. Lyons, Aust. J. Chem. 1980, 33, 1717-1725.
    • (1980) Aust. J. Chem. , vol.33 , pp. 1717-1725
    • Lyons, L.E.1
  • 58
    • 2142839976 scopus 로고    scopus 로고
    • note
    • -1.
  • 59
    • 2142837426 scopus 로고    scopus 로고
    • note
    • However, the values obtained to estimate the behavior of the molecule in solution should be used with caution since the solvation energy was not taken into account.
  • 60
    • 2142668471 scopus 로고    scopus 로고
    • note
    • -1: (Ε′ was determined in supposition of the intramolecular absorption).
  • 64
    • 0002646558 scopus 로고
    • (Ed.: B. Scrosati). Chapman & Hall, London. Chapter 7
    • M. Mastragostino, in Electrochromic Devices (Ed.: B. Scrosati). Chapman & Hall, London 1993, Chapter 7, pp. 223-249.
    • (1993) Electrochromic Devices , pp. 223-249
    • Mastragostino, M.1
  • 65
    • 2142833667 scopus 로고    scopus 로고
    • note
    • Appearance of the same bands was observed by electrochemical oxidation of TTF derivative 11 (Figure S7).
  • 66
    • 2142847576 scopus 로고    scopus 로고
    • note
    • The assignment of these bands is supported by spectroelectrochemical experiments on the fluorene derivative 6 (Figure S8) and the electronic spectra of isolated fluorene ion-radical salt 24.
  • 76
    • 0004150157 scopus 로고    scopus 로고
    • Bruker AXS Inc., Madison, Wisconsin, USA
    • SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA, 1998.
    • (1998) SHELXTL. Version 5.1
  • 78
    • 2142731443 scopus 로고    scopus 로고
    • note
    • The yield could possibly be improved by using 5-10 times lower concentration.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.