Home > Research > Publications & Outputs > A Functionalized 8 nm Long Aryleneethynylene Mo...

Research

Associated organisational unit

Electronic data

Links

Text available via DOI:

Keywords

View graph of relations

A Functionalized 8 nm Long Aryleneethynylene Molecular Wire with Alkyne Termini.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Published

Standard

A Functionalized 8 nm Long Aryleneethynylene Molecular Wire with Alkyne Termini. / Zeng, Xianshun; Wang, Changsheng; Bryce, Martin R. et al.
In: European Journal of Organic Chemistry, Vol. 2007, No. 31, 11.2007, p. 5244-5249.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Zeng, X, Wang, C, Bryce, MR, Batsanov, AS, Sirichantaropass, S, Garcia Suarez, VM, Lambert, CJ & Sage, I 2007, 'A Functionalized 8 nm Long Aryleneethynylene Molecular Wire with Alkyne Termini.', European Journal of Organic Chemistry, vol. 2007, no. 31, pp. 5244-5249. https://doi.org/10.1002/ejoc.200700507

APA

Zeng, X., Wang, C., Bryce, M. R., Batsanov, A. S., Sirichantaropass, S., Garcia Suarez, V. M., Lambert, C. J., & Sage, I. (2007). A Functionalized 8 nm Long Aryleneethynylene Molecular Wire with Alkyne Termini. European Journal of Organic Chemistry, 2007(31), 5244-5249. https://doi.org/10.1002/ejoc.200700507

Vancouver

Zeng X, Wang C, Bryce MR, Batsanov AS, Sirichantaropass S, Garcia Suarez VM et al. A Functionalized 8 nm Long Aryleneethynylene Molecular Wire with Alkyne Termini. European Journal of Organic Chemistry. 2007 Nov;2007(31):5244-5249. doi: 10.1002/ejoc.200700507

Author

Zeng, Xianshun ; Wang, Changsheng ; Bryce, Martin R. et al. / A Functionalized 8 nm Long Aryleneethynylene Molecular Wire with Alkyne Termini. In: European Journal of Organic Chemistry. 2007 ; Vol. 2007, No. 31. pp. 5244-5249.

Bibtex

@article{0edaa25e82a54d558a78cf294eebbe5f,
title = "A Functionalized 8 nm Long Aryleneethynylene Molecular Wire with Alkyne Termini.",
abstract = "The synthesis of new conjugated aryleneethynylene derivatives of up to ca. 8 nm molecular length (compound 16) with terminal alkyne substituents and 9,9-dihexylfluorene units in the backbone is described. Key synthetic steps are Pd-mediated Sonogashira coupling methodology combined with regioselective removal from the terminal alkyne units of 2-hydroxy-2-propyl protecting groups in the presence of trimethylsilyl groups. The structural and electronic properties of 16 were obtained from DFT calculations: the intramolecular terminal C···C distance in its relaxed conformation was found to be 7.8 nm. The calculated distribution of HOMO and LUMO orbitals and the strong blue fluorescence observed for 16 (max = 420, 443 nm in CHCl3 solution) are consistent with a highly conjugated penta[(9,9-dihexyl-2,7-fluorenylene)ethynylene] structure. Molecule 16 possesses multifunctionality and is of interest for future molecular electronic device applications.",
keywords = "Molecular wires , Fluorene , Sonogashira reaction , Aryleneethynylene",
author = "Xianshun Zeng and Changsheng Wang and Bryce, {Martin R.} and Batsanov, {Andrei S.} and Skon Sirichantaropass and {Garcia Suarez}, {Victor M.} and Lambert, {Colin J.} and Ian Sage",
note = "This is a pre-print of an article published in European Journal of Organic Chemistry, 2007 (31), 2007. (c) Wiley.",
year = "2007",
month = nov,
doi = "10.1002/ejoc.200700507",
language = "English",
volume = "2007",
pages = "5244--5249",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-VCH Verlag",
number = "31",

}

RIS

TY - JOUR

T1 - A Functionalized 8 nm Long Aryleneethynylene Molecular Wire with Alkyne Termini.

AU - Zeng, Xianshun

AU - Wang, Changsheng

AU - Bryce, Martin R.

AU - Batsanov, Andrei S.

AU - Sirichantaropass, Skon

AU - Garcia Suarez, Victor M.

AU - Lambert, Colin J.

AU - Sage, Ian

N1 - This is a pre-print of an article published in European Journal of Organic Chemistry, 2007 (31), 2007. (c) Wiley.

PY - 2007/11

Y1 - 2007/11

N2 - The synthesis of new conjugated aryleneethynylene derivatives of up to ca. 8 nm molecular length (compound 16) with terminal alkyne substituents and 9,9-dihexylfluorene units in the backbone is described. Key synthetic steps are Pd-mediated Sonogashira coupling methodology combined with regioselective removal from the terminal alkyne units of 2-hydroxy-2-propyl protecting groups in the presence of trimethylsilyl groups. The structural and electronic properties of 16 were obtained from DFT calculations: the intramolecular terminal C···C distance in its relaxed conformation was found to be 7.8 nm. The calculated distribution of HOMO and LUMO orbitals and the strong blue fluorescence observed for 16 (max = 420, 443 nm in CHCl3 solution) are consistent with a highly conjugated penta[(9,9-dihexyl-2,7-fluorenylene)ethynylene] structure. Molecule 16 possesses multifunctionality and is of interest for future molecular electronic device applications.

AB - The synthesis of new conjugated aryleneethynylene derivatives of up to ca. 8 nm molecular length (compound 16) with terminal alkyne substituents and 9,9-dihexylfluorene units in the backbone is described. Key synthetic steps are Pd-mediated Sonogashira coupling methodology combined with regioselective removal from the terminal alkyne units of 2-hydroxy-2-propyl protecting groups in the presence of trimethylsilyl groups. The structural and electronic properties of 16 were obtained from DFT calculations: the intramolecular terminal C···C distance in its relaxed conformation was found to be 7.8 nm. The calculated distribution of HOMO and LUMO orbitals and the strong blue fluorescence observed for 16 (max = 420, 443 nm in CHCl3 solution) are consistent with a highly conjugated penta[(9,9-dihexyl-2,7-fluorenylene)ethynylene] structure. Molecule 16 possesses multifunctionality and is of interest for future molecular electronic device applications.

KW - Molecular wires

KW - Fluorene

KW - Sonogashira reaction

KW - Aryleneethynylene

U2 - 10.1002/ejoc.200700507

DO - 10.1002/ejoc.200700507

M3 - Journal article

VL - 2007

SP - 5244

EP - 5249

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 31

ER -