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Volumn 2, Issue 6, 1996, Pages 624-633

Self-assembling tetrathiafulvalene-based rotaxanes and catenanes

Author keywords

Catenanes; Macrocycles; Rotaxanes; Self assembly; Tetrathiafulvalenes

Indexed keywords

CATENANES; ELECTROSPRAY MASS SPECTROMETRY; HEXAFLUOROPHOSPHATES; MACROCYCLES; ROTAXANES; STACKING INTERACTION; SUPRAMOLECULAR STRUCTURE; TETRATHIAFULVALENES;

EID: 0000647283     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.19960020605     Document Type: Article
Times cited : (86)

References (105)
  • 63
    • 0002540616 scopus 로고
    • For reviews on TTF supramolecular chemistry, see a
    • For reviews on TTF supramolecular chemistry, see a) T. Jørgensen, T. K. Hansen, J. Becher, Chem. Soc. Rev. 1994, 23, 41;
    • (1994) Chem. Soc. Rev. , vol.23 , pp. 41
    • Jørgensen, T.1    Hansen, T.K.2    Becher, J.3
  • 73
    • 0028963065 scopus 로고
    • For a review on the chemistry of 1,3-dithiole-2-thione-4,5.dithiolate, see
    • For a review on the chemistry of 1,3-dithiole-2-thione-4,5.dithiolate, see N. Svenstrup, J. Becher, Synthesis 1995, 215.
    • (1995) Synthesis , pp. 215
    • Svenstrup, N.1    Becher, J.2
  • 79
    • 84891303885 scopus 로고    scopus 로고
    • note
    • TTF-containing macrocyclic compounds have been synthesized in most cases by using a coupling reaction in the presence of trialkyl phosphites from the corresponding thiones (see ref. [11] and [13]). There are only few reports describing the synthesis of TTF-derived macrocyclic systems directly starting from TTF-containing precursors (see ref. [11 a]).
  • 81
    • 0001682263 scopus 로고
    • Some of the results discussed in this paper have been mentioned in a preliminary communication
    • Some of the results discussed in this paper have been mentioned in a preliminary communication: Z.-T. Li, P. C. Stein, N. Svenstrup, K. H. Lund, J. Becher, Angew. Chem. 1995, 107, 2719;
    • (1995) Angew. Chem. , vol.107 , pp. 2719
    • Li, Z.-T.1    Stein, P.C.2    Svenstrup, N.3    Lund, K.H.4    Becher, J.5
  • 83
    • 84891329149 scopus 로고    scopus 로고
    • note
    • This chain had been proved suitable for preparing a 1,4-dioxyphenylene- based rotaxane (see ref. [6b]).
  • 87
    • 84891318356 scopus 로고    scopus 로고
    • note
    • The mixtures of isomers could not be separated because they slowly isomerized to each other in solution containing trace amounts of acid (detected by TLC). In all the reactions leading to the monomacrocyclic compounds 7a-d, no 2,3-deprotection-cyclization products were detected (TLC indicated that no other major products were formed except the insoluble linear oligomers), although tetrathiafulvalene-2,3,6,7-tetrathiolate could be produced quantitatively from 6 in the presence of 8 equiv of cesium hydroxide (see ref. [20]).
  • 88
    • 84891333105 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum indicated that the ratio of the cis and trans isomers is about 5:1, based on the integration of the two phenylene proton signals.
  • 89
    • 84891331040 scopus 로고    scopus 로고
    • note
    • Recently, [2]catenanes incorporating a bis(2-oxy-1,3-propylenedithio) tetrathiafulvalene unit and a 1,4-bis(oxymethyl)phenylene unit have been synthesized by Prof. Stoddart's group. We thank Dr. G. Mattersteig and Prof. J. F. Stoddart for providing the information.
  • 92
    • 84891302795 scopus 로고    scopus 로고
    • note
    • Quantitative synthesis of [2]catenanes has been reported recently by utilizing the labile nature of a palladium or platinum(II)-pyridine coordinate bond, in which Pd or Pt metal centers are part of the macrocycles but do not intervene during the catenation (see ref. [4a]).
  • 93
    • 84891284679 scopus 로고    scopus 로고
    • note
    • Unsymmetrical TTF compounds usually isomerize readily, catalyzed by trace amounts of acid. Two methods have been used to control the configurational isomerization of TTF macrocyclic compounds. The first utilized the difference between the ring strains of the cis/trans isomers (see ref. [11c] and [13]). The second approach involved one-electron oxidation of [12]- and [14]tetrathiafulvalenophanes (see ref. [11 d]). However, in all these cases the planarity of the neutral TTF subunits was destroyed by the short chains linking the opposite ends of the TTF groups.
  • 104
    • 84891294761 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra (based on the integration of the two sets of aromatic proton signals).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.