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Volumn 126, Issue 37, 2004, Pages 11500-11508

Phototriggered self-assembly of hydrogen-bonded rosette

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHY; COMPLEXATION; HYDROGEN BONDS; IRRIGATION; LIGHT SCATTERING; MIXTURES; MONOMERS; SELF ASSEMBLY; SYNTHESIS (CHEMICAL);

EID: 4544227362     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047783z     Document Type: Article
Times cited : (95)

References (119)
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    • For examples of azobenzene-incorporated lipids, vesicles, micelles, and bilayers, see: (a) Kuiper, J. M.; Engberts, J. B. F. N. Langmuir 2004, 20, 1152-1160.
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    • For examples of azobenzene-incorporated liquid crystalline materials, see: (a) Ichimura, K. Chem. Rev. 2000, 100, 1847-1873.
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    • Ichimura, K.1
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    • 1942454902 scopus 로고    scopus 로고
    • For examples of azobenzene-incorporated Langmuir-Brodgett films, see: (a) Azumi, R.; Kakiuchi, K.; Matsumoto, M. Chem. Lett. 2004, 33, 172-173.
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    • Azumi, R.1    Kakiuchi, K.2    Matsumoto, M.3
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    • 2442636331 scopus 로고    scopus 로고
    • For examples of an azobenzene-incorporated host-guest complex, see: (a) Otsuki, J.; Narutaki, K.; Bakke, J. M. Chem. Lett. 2004, 33, 356-357.
    • (2004) Chem. Lett. , vol.33 , pp. 356-357
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    • note
    • Recently, Sleiman et al. reported cyclicletrarrier of (Z)-azodibenzoic acid derivatives that hierarchically grow into a rodlike edifice by π-π stacking (see ref 3a)
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    • note
    • 1H NMR spectrum.
  • 88
    • 4544286536 scopus 로고    scopus 로고
    • note
    • The rosette composed of TDP-lacking M1 and B1 did not elute from the SEC column because it decomposed during the analysis and the resulting components were adsorbed to the column matrix.
  • 89
    • 0034607371 scopus 로고    scopus 로고
    • Similar overestimations have been reported in the SEC analyses of structurally related azobenzene-containing dendrons possessing a large number of long alkyl chains: (a) Yokoyama, S.; Nakahama, T.; Otomo, A.; Mashiko, S. J. Am. Chem. Soc. 2000, 122, 3174-4181.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 3174-4181
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  • 95
    • 4544336019 scopus 로고    scopus 로고
    • note
    • Because of the self-aggregation property of B2, the signals of the imide protons (signals k and l) of the residual B2 shifted to low field with its increasing concentration.
  • 100
    • 0001226628 scopus 로고    scopus 로고
    • (b) Freeman, A. W.; Vreekamp, R. H.; Fréchet, J. M. J. Polym. Mater. Sci. Eng. 1997, 77, 138-139. In the former two systems, an increase in the generation of dendrons resulted in a decrease in the stability of the self-assembling dendrimers by gaining a steric interaction between them.
    • (1997) Polym. Mater. Sci. Eng. , vol.77 , pp. 138-139
    • Freeman, A.W.1    Vreekamp, R.H.2    Fréchet, J.M.J.3
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    • Würthner et al. reported the liquid-crystalline bulk materials composed of coaggregates of TDP-attached melamine and merocyanine-type barbiturate, both structurally related to M2 and B2, respectively: Würthner, F.; Yao, S.; Heise, B.; Tschierske, C. Chem. Commun. 2001, 2260-2261. In this case, a linear tapelike assembly was deduced from the XPD studies.
    • (2001) Chem. Commun. , pp. 2260-2261
    • Würthner, F.1    Yao, S.2    Heise, B.3    Tschierske, C.4
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    • note
    • One of the reviewers suggested that the present rosette can be called "monodisperse inverse micelles" when taking into account that the exterior alkyl chains are not stretched in an all-transoid conformation.
  • 104
    • 0037123782 scopus 로고    scopus 로고
    • The association constant for the melamine-barbiturate complexation has proved to be 2 orders of magnitude lower than that for the melamine-cyanurate complexation: (a) Prins, L. J.; Verhage, J. J.; de Jong, F.; Timmerman, P.; Reinhoudt, D. N. Chem.-Eur. J. 2002, 8, 2302-2313.
    • (2002) Chem.-Eur. J. , vol.8 , pp. 2302-2313
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    • note
    • For details, see Supporting Information.
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    • In this experiment, a small proportion of the intermediate species EZ-M2 for any irradiation time strongly suggests the cooperative E → Z isomerization of the two azobenzene moieties of EE-M2; isomerization of one of the two E-azobenzene moieties promotes subsequent isomerization of another one: (a) Itoho, K.; Masuda, T.; Takei, M.; Sakurai, Y.; Nishigami, M. J. Chem. Soc., Chem. Commun. 1986, 1028-1030.
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    • note
    • As one of the reviewers pointed out, a rosette might be formed if at least some EZ-M2 molecules are involved in the rosette with ZZ-M2. In other words, ZZ-M2 alone could not form a rosette with B2. This suggestion is fully consistent with the result of the molecular modeling study as well as the result of the phototriggered SEC experiment described below.
  • 119
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    • note
    • A similar steric argument was done for the self-assembling dendrimers: see refs 16 and 30.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.