Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes

Fang Lin; Hai Yan Peng; Jing Xing Chen; David T.W. Chik; Zongwei CAI; Keith M.C. Wong; Vivian W.W. Yam; Henry N.C. Wong

doi:10.1021/ja106599j

Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes

Fang Lin, Hai Yan Peng, Jing Xing Chen, David T.W. Chik, Zongwei CAI, Keith M.C. Wong, Vivian W.W. Yam, Henry N.C. Wong

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

50 Citations (Scopus)

Abstract

This paper is concerned with the synthesis and reactions of enantiopure 1,8,9,16-tetraethynyltetraphenylene (3). We obtained 3 in 34% yield through four steps starting from 1,8,9,16-tetrahydroxytetraphenylene (2a) via a functional group interconversion strategy. On the basis of this chiral "helical" building block, three rigid helical macrocycles 14, 15, and 22 were designed. Complexes 14 and 15 were constructed via coordination-driven self-assembly with platinum(II) complexes 8 and 9b, while 22 cannot be obtained successfully. Then macrocycle 28 was designed on the structural basis of 22 to which octyl chains were introduced, in the hope of improving the solubility of the complex. Macrocycle 28 was finally formed and was characterized by NMR spectroscopy, elemental analysis, and electrospray mass spectrometry. For the enantiopure 15 and 28, circular dichroism (CD) spectra also exhibited chiral properties. Complexes 27 and 28 both exhibited an intense emission band at 621 nm in acetonitrile at 298 K upon excitation at λ > 420 nm.

Original language	English
Pages (from-to)	16383-16392
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	132
Issue number	46
DOIs	https://doi.org/10.1021/ja106599j
Publication status	Published - 24 Nov 2010

Scopus Subject Areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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Lin, F., Peng, H. Y., Chen, J. X., Chik, D. T. W., CAI, Z., Wong, K. M. C., Yam, V. W. W., & Wong, H. N. C. (2010). Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes. Journal of the American Chemical Society, 132(46), 16383-16392. https://doi.org/10.1021/ja106599j

Lin, Fang ; Peng, Hai Yan ; Chen, Jing Xing et al. / Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes. In: Journal of the American Chemical Society. 2010 ; Vol. 132, No. 46. pp. 16383-16392.

@article{5d233983bd954d08b16c6a55bf094c69,

title = "Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes",

abstract = "This paper is concerned with the synthesis and reactions of enantiopure 1,8,9,16-tetraethynyltetraphenylene (3). We obtained 3 in 34% yield through four steps starting from 1,8,9,16-tetrahydroxytetraphenylene (2a) via a functional group interconversion strategy. On the basis of this chiral {"}helical{"} building block, three rigid helical macrocycles 14, 15, and 22 were designed. Complexes 14 and 15 were constructed via coordination-driven self-assembly with platinum(II) complexes 8 and 9b, while 22 cannot be obtained successfully. Then macrocycle 28 was designed on the structural basis of 22 to which octyl chains were introduced, in the hope of improving the solubility of the complex. Macrocycle 28 was finally formed and was characterized by NMR spectroscopy, elemental analysis, and electrospray mass spectrometry. For the enantiopure 15 and 28, circular dichroism (CD) spectra also exhibited chiral properties. Complexes 27 and 28 both exhibited an intense emission band at 621 nm in acetonitrile at 298 K upon excitation at λ > 420 nm.",

author = "Fang Lin and Peng, {Hai Yan} and Chen, {Jing Xing} and Chik, {David T.W.} and Zongwei CAI and Wong, {Keith M.C.} and Yam, {Vivian W.W.} and Wong, {Henry N.C.}",

note = "Dedicated to Professor Eiichi Nakamura on the occasion of his 60th birthday. The Institute of Molecular Functional Materials is an Area of Excellence under the University Grants Committee (Hong Kong). This work was supported by a grant from the Croucher Foundation (Hong Kong), a General Research Fund from Research Grants Council (Hong Kong) (RGC ref. No. CUHK403909), the External Cooperation Program of the Chinese Academy of Sciences (BGrant No GJHZ200816), and the University Grants Committee Areas of Excellence Scheme (AoE/P-03/08). F.L. acknowledges with thanks the Croucher Foundation (Hong Kong) for a Shanghai Studentship. The Science and Technology Commission of the Shanghai Municipal Government also partially supported this program. We thank Professors Li-Xin Dai and Xue-Long Hou for helpful discussions. ",

year = "2010",

month = nov,

day = "24",

doi = "10.1021/ja106599j",

language = "English",

volume = "132",

pages = "16383--16392",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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}

Lin, F, Peng, HY, Chen, JX, Chik, DTW, CAI, Z, Wong, KMC, Yam, VWW & Wong, HNC 2010, 'Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes', Journal of the American Chemical Society, vol. 132, no. 46, pp. 16383-16392. https://doi.org/10.1021/ja106599j

Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes. / Lin, Fang; Peng, Hai Yan; Chen, Jing Xing et al.
In: Journal of the American Chemical Society, Vol. 132, No. 46, 24.11.2010, p. 16383-16392.

Research output: Contribution to journal › Journal article › peer-review

TY - JOUR

T1 - Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes

AU - Lin, Fang

AU - Peng, Hai Yan

AU - Chen, Jing Xing

AU - Chik, David T.W.

AU - CAI, Zongwei

AU - Wong, Keith M.C.

AU - Yam, Vivian W.W.

AU - Wong, Henry N.C.

N1 - Dedicated to Professor Eiichi Nakamura on the occasion of his 60th birthday. The Institute of Molecular Functional Materials is an Area of Excellence under the University Grants Committee (Hong Kong). This work was supported by a grant from the Croucher Foundation (Hong Kong), a General Research Fund from Research Grants Council (Hong Kong) (RGC ref. No. CUHK403909), the External Cooperation Program of the Chinese Academy of Sciences (BGrant No GJHZ200816), and the University Grants Committee Areas of Excellence Scheme (AoE/P-03/08). F.L. acknowledges with thanks the Croucher Foundation (Hong Kong) for a Shanghai Studentship. The Science and Technology Commission of the Shanghai Municipal Government also partially supported this program. We thank Professors Li-Xin Dai and Xue-Long Hou for helpful discussions.

PY - 2010/11/24

Y1 - 2010/11/24

N2 - This paper is concerned with the synthesis and reactions of enantiopure 1,8,9,16-tetraethynyltetraphenylene (3). We obtained 3 in 34% yield through four steps starting from 1,8,9,16-tetrahydroxytetraphenylene (2a) via a functional group interconversion strategy. On the basis of this chiral "helical" building block, three rigid helical macrocycles 14, 15, and 22 were designed. Complexes 14 and 15 were constructed via coordination-driven self-assembly with platinum(II) complexes 8 and 9b, while 22 cannot be obtained successfully. Then macrocycle 28 was designed on the structural basis of 22 to which octyl chains were introduced, in the hope of improving the solubility of the complex. Macrocycle 28 was finally formed and was characterized by NMR spectroscopy, elemental analysis, and electrospray mass spectrometry. For the enantiopure 15 and 28, circular dichroism (CD) spectra also exhibited chiral properties. Complexes 27 and 28 both exhibited an intense emission band at 621 nm in acetonitrile at 298 K upon excitation at λ > 420 nm.

AB - This paper is concerned with the synthesis and reactions of enantiopure 1,8,9,16-tetraethynyltetraphenylene (3). We obtained 3 in 34% yield through four steps starting from 1,8,9,16-tetrahydroxytetraphenylene (2a) via a functional group interconversion strategy. On the basis of this chiral "helical" building block, three rigid helical macrocycles 14, 15, and 22 were designed. Complexes 14 and 15 were constructed via coordination-driven self-assembly with platinum(II) complexes 8 and 9b, while 22 cannot be obtained successfully. Then macrocycle 28 was designed on the structural basis of 22 to which octyl chains were introduced, in the hope of improving the solubility of the complex. Macrocycle 28 was finally formed and was characterized by NMR spectroscopy, elemental analysis, and electrospray mass spectrometry. For the enantiopure 15 and 28, circular dichroism (CD) spectra also exhibited chiral properties. Complexes 27 and 28 both exhibited an intense emission band at 621 nm in acetonitrile at 298 K upon excitation at λ > 420 nm.

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U2 - 10.1021/ja106599j

DO - 10.1021/ja106599j

M3 - Journal article

AN - SCOPUS:78649259654

SN - 0002-7863

VL - 132

SP - 16383

EP - 16392

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 46

ER -

Lin F, Peng HY, Chen JX, Chik DTW, CAI Z, Wong KMC et al. Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes. Journal of the American Chemical Society. 2010 Nov 24;132(46):16383-16392. doi: 10.1021/ja106599j

Synthesis and photophysical studies of chiral helical macrocyclic scaffolds via coordination-driven self-assembly of 1,8,9,16-tetraethynyltetraphenylene. Formation of monometallic platinum(II) and dimetallic platinum(II)-ruthenium(II) complexes

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