메뉴 건너뛰기




Volumn 9, Issue 19, 2003, Pages 4771-4780

Photoresponsive supramolecular systems: Self-assembly of azodibenzoic acid linear tapes and cyclic tetramers

Author keywords

Azobenzene; Hydrogen bonds; Photochromism; Self assembly; Supramolecular chemistry

Indexed keywords

BENZENE; HYDROGEN BONDS; ISOMERIZATION; SELF ASSEMBLY;

EID: 0142087759     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200304864     Document Type: Article
Times cited : (92)

References (71)
  • 18
    • 0033152135 scopus 로고    scopus 로고
    • a) M. S. Vollmer, T. D. Clark, C. Steinem, M. R. Ghadiri, Angew. Chem. 1999, 111, 1703-1706; Angew. Chem. Int. Ed. 1999, 38, 1598-1601;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 1598-1601
  • 20
    • 0035857549 scopus 로고    scopus 로고
    • b) D. T. Bong, T. D. Clark, J. R. Ganja, M. R. Ghadiri, Angew. Chem. 2001, 113, 1016-1041; Angew. Chem. Int. Ed. 2001, 40, 988-1011.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 988-1011
  • 22
    • 0033549733 scopus 로고    scopus 로고
    • H. Asanuma, T. Ito, T. Yoshida, X. Liang, M. Komiyama, Angew. Chem. 1999, 111, 2547-2549; Angew. Chem. Int. Ed. 1999, 38, 2393-2395.
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 2393-2395
  • 26
    • 0345850194 scopus 로고    scopus 로고
    • a) K. Ichimura, Chem. Rev. 2000, 100, 1847-1873;
    • (2000) Chem. Rev. , vol.100 , pp. 1847-1873
    • Ichimura, K.1
  • 31
    • 0004264875 scopus 로고    scopus 로고
    • (Eds.: H. J. Coufal, D. Psaltis, G. T. Sincerbox), Springer, Berlin, Heidelberg
    • c) Holographic Data Storage (Eds.: H. J. Coufal, D. Psaltis, G. T. Sincerbox), Springer, Berlin, Heidelberg, 2000.
    • (2000) Holographic Data Storage
  • 38
    • 0142109793 scopus 로고    scopus 로고
    • note
    • d) the C-N=N angle obtained by our PM3 calculations for cis-p-azodibenzoic acid (126.9°), cis-o-bis(methoxy)-p-azodibenzoic acid (127.2°), cis-o-bis(decyloxy)-p-azodibenzoic acid (127.8°) agrees with experimental X-ray results for o-substituted cis-azobenzene (126.4°) (see ref. [20]). The details of these calculations will be published elsewhere.
  • 39
    • 0142046324 scopus 로고    scopus 로고
    • note
    • See Supporting Information.
  • 40
    • 0142046325 scopus 로고    scopus 로고
    • note
    • Similar PM3 calculations were performed on hydrogen-bonded isophthalic acid aggregates. These theoretical studies agree with experimental evidence, showing that the unsubstituted isophthalic acid form tapes instead of rosettes (see ref. [3a,b]), thus validating our predictions.
  • 41
    • 0142078203 scopus 로고    scopus 로고
    • note
    • Attempts to form cyclic cis-azodibenzoic acid trimers by using PM3 only yielded the open aggregates. A triangle was obtained from HF/STO-3G monomers, which were then assembled to form the desired structure, then optimized using PM3. This optimization gave a triangle with bent hydrogen-bonds, which were weaker than in the larger macrocycles and in the open aggregates.
  • 47
    • 0037124694 scopus 로고    scopus 로고
    • e) A. Lützen, M. M. Hapke, J. Griep-Raming, D. Haase, W. Saak, Angew. Chem. 2002, 114, 2190-2194; Angew. Chem. Int. Ed. 2002, 41, 2086-2089.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 2086-2089
  • 49
    • 0142046322 scopus 로고    scopus 로고
    • note
    • 2|. CCDC-184609 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; (fax: (+44) 1223-336-033; or e-mail: deposit@ccdc.cam.ac.uk);
  • 50
    • 0003872738 scopus 로고
    • Tables 4.2.6.8 and 6.1.1.4 Kluwer, Dordrecht
    • b) International Tables for Crystallography, Vol. C, Tables 4.2.6.8 and 6.1.1.4 Kluwer, Dordrecht, 1992;
    • (1992) International Tables for Crystallography , vol.100
  • 60
    • 0142014487 scopus 로고    scopus 로고
    • note
    • a) When the diffraction pattern of trans-1 was substracted from the diffraction pattern of cis-2, the main diffraction peak appeared as one single peak. The peaks at 14.0, 24.0, 25.7 and 27.0° correspond to Bragg spacings of 0.73, 0.43, 0.40, and 0.38 nm, respectively. These dimensions may be related to the distance between two stacked cyclic tetramers of cis-2;
  • 63
    • 0142014485 scopus 로고    scopus 로고
    • note
    • This diameter was estimated from the PM3 optimized structure of the cis-azodibenzoic acid tetramer (Ø = 2.31 nm) onto which were super-imposed four optimized decyloxy-substituted monomers. The distance between two opposite chain-ends was measured directly. See Supporting Information.
  • 64
    • 0142014481 scopus 로고    scopus 로고
    • note
    • -1), the VPO data points lie slightly below the regression curves, suggesting the preponderance of monomeric species in such dilute solutions (See Supporting Information). However, at higher concentrations, the results are consistent with supramolecular tetramers.
  • 65
    • 0142014486 scopus 로고    scopus 로고
    • note
    • + calculations show that the orientation of the aromatic rings in the macrocycle and the position of the alkoxy chains can favor the efficient stacking of these tetrameric macrocycles into rod-like morphologies. The details of these calculations will be published elsewhere.
  • 66
    • 0142078202 scopus 로고    scopus 로고
    • note
    • See Experimental Section for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.