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Volumn 14, Issue 18, 2008, Pages 5680-5686

An Hg2+-gated chiral molecular switch created by using binaphthalene molecules with two anthracene units and two 1,3-dithiole-2-thione (1,3-dithiole-2-one) units

Author keywords

Anthracene; Binaphthalene; Circular dichroism; Dimerization; Molecular switches

Indexed keywords

ANTHRACENE; DICHROISM; KETONES; MERCURY (METAL); OPTICAL PROPERTIES;

EID: 53849110295     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800216     Document Type: Article
Times cited : (22)

References (55)
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    • We have recently reported the quenching of the excited state of anthracene within a tetrathiafulvalene-anthracene dyad. This excited state can be activated by oxidation or assembly on the surfaces of gold nanoparlicles, which leads to fluorescence enhancement and facilitalion of the photodimerization process: a G. X. Zhang, D. Q. Zhang, X. F. Guo, D. B. Zhu, Org. Lett. 2004, 6, 1209-1212
    • We have recently reported the quenching of the excited state of anthracene within a tetrathiafulvalene-anthracene dyad. This excited state can be "activated" by oxidation or assembly on the surfaces of gold nanoparlicles, which leads to fluorescence enhancement and facilitalion of the photodimerization process: a) G. X. Zhang, D. Q. Zhang, X. F. Guo, D. B. Zhu, Org. Lett. 2004, 6, 1209-1212:
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    • It was reported that the optically active 2.2′-substituted binaphthalene enantiomer was very stable and could not be racemized at high temperatures (> 150°C). see: a) D. M. Hall, E. E. Turner, J. Chem. Soc. 1955, 1242-1251;
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    • The detected fluorescence of (S)-1 and (S)-2 should be due to the anthracene units because the excitation wavelength is 370 nm, at which binaphthalene does not absorb. The corresponding fluorescence quantum yields were estimated by reference to 9,10-diphenyl-anthracene.
    • The detected fluorescence of (S)-1 and (S)-2 should be due to the anthracene units because the excitation wavelength is 370 nm, at which binaphthalene does not absorb. The corresponding fluorescence quantum yields were estimated by reference to 9,10-diphenyl-anthracene.
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    • The biexponential fluorescence decay of (S)-1 can be interpreted as follows: 1)when the anthracene units of (S)-1 are excited by UV light irradiation (Λcx=370nm, two excited species may be formed, in which the two anthracene units may exhibit different orientations in relation to the naphthalene and 1,3-dithole-2-thione units: 2) it is probable that in one excited species the anthracene units are close to 1,3-dilhole-2-thione units (and naphthalene units) and as a result, the fluorescence from this excited species would be largely quenched, which would lead to a rather short fluorescence lifetime; whereas in another excited species the anthracene units are well separated from 1,3-dithole-2-thione units (and naphthalene units, and accordingly the fluorescence from this excited species would not be quenched to a large extent. In fact, biexponential fluorescence decay was reported previously for the TTF-naphthalenediimide-TTF triad see X. G
    • cx=370nm), two excited species may be formed, in which the two anthracene units may exhibit different orientations in relation to the naphthalene and 1,3-dithole-2-thione units: 2) it is probable that in one excited species the anthracene units are close to 1,3-dilhole-2-thione units (and naphthalene units) and as a result, the fluorescence from this excited species would be largely quenched, which would lead to a rather short fluorescence lifetime; whereas in another excited species the anthracene units are well separated from 1,3-dithole-2-thione units (and naphthalene units), and accordingly the fluorescence from this excited species would not be quenched to a large extent. In fact, biexponential fluorescence decay was reported previously for the TTF-naphthalenediimide-TTF triad (see X. Guo, Z. Gan, H. Luo, Y. Araki, D. Zhang, D. Zhu, O. Ito, J. Phys. Chem. A 2003, 107, 9747-9753). The solute-solvent interaction might also cause a biexponential fluorescence decay
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    • Many metal ions including Ag, Pb2, Cu 2, Zn2, Fe3, Fe2, Co 2, and Ni2+ have been tried; only Hg2+ can easily induce the transformation of 1,3-dithiole-2-thione into 1,3-dithiole-2-one at room temperature. Compound (S)-1 (1.1 mg) was reacted with Hg(AcO)2 (1.9 mg) in CH2Cl2 (2mL) for 5 min at room temperature. After that, 40 μL of the reaction solution was diluted with THF (2 mL) for spectral measurements. The fluorescence quantum yield of this solution of (S)-I after reaction with Hg(AcO)2 was determined to be 0.054, lower than that of (S)-2 (0.11, The corresponding fluorescence decay can be well fitted with a single-exponential function; the fluorescence lifetime was estimated to be 3.27 ns, see Figure S3a, This is slightly shorter than that of (S)-2 3.54 ns, The quenching e
    • 2 and (S)-2.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.