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