Organotin compounds bearing mesogenic sidechains: synthesis, x-ray structures and polymerisation chemistry

P R Deacon, N Devylder, M S Hill, M F Mahon, K C Molloy, G J Price

Research output: Contribution to journalArticle

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Abstract

Organotin compounds R3Sn(CH2)(n+2)OC6H4C6H4Y (R-3 = Ph-3, Ph2Bu; Y = H, CN; n = 1-3) and RX2Sn(CH2)(n+2)OC6H4C6H4Y (R = Ph, Bu; Y = H, CN; X = Br, I; n = 1-3) have been synthesised and characterised by H-1-, C-13-, Sn-119-NMR and Mossbauer spectroscopies. X-ray crystallography reveals tetrahedral geometries for Ph3Sn(CH2)(4)OC6H4C6H5 and Ph3Sn(CH2)(3)OC6H4C6H4CN, a six-coordinated, bromine-bridged dimeric structure for PhBr2Sn(CH2)(3)OC6H4C6H5 containing a mer-Br3C2OSn coordination sphere about tin and a five-coordinated monomeric structure for PhBr2Sn(CH2)3OC6H4C6H4CN. In all cases there is strong alignment of mesogenic groups in the solid-state but only PhBr2Sn(CH2)(3)OC6H4C6H4CN shows any indication of liquid-crystal behaviour. Wurtz polymerisation of RBr2Sn(CH2)(5)OC6H4C6H5 (R = Ph, Bu), both of which contain non-chelating ether functions, generated polystannanes (RR'Sn)(n) with M-n 2.3 x 10(5); M-w 3.0 x 10(5); M-w/M-n 1.30 and M-n 1.3 x 10(5); M-w 2.5 x 10(5); M-w/M-n 1.96, respectively, while no polymer was obtained from chelated PhBr2Sn(CH2)(3)OC6H4C6H5 (C) 2003 Elsevier B.V. All rights reserved.
LanguageEnglish
Pages46-56
Number of pages11
JournalJournal of Organometallic Chemistry
Volume687
Issue number1
DOIs
StatusPublished - 2003

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Bearings (structural)
Organotin Compounds
Bromine
Liquid Crystals
Tin
X ray crystallography
Mossbauer spectroscopy
Polymerization
Ether
Liquid crystals
Nuclear magnetic resonance spectroscopy
Ethers
Polymers
polymerization
X-Rays
chemistry
X rays
Geometry
synthesis
Mossbauer Spectroscopy

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Organotin compounds bearing mesogenic sidechains: synthesis, x-ray structures and polymerisation chemistry. / Deacon, P R; Devylder, N; Hill, M S; Mahon, M F; Molloy, K C; Price, G J.

In: Journal of Organometallic Chemistry, Vol. 687, No. 1, 2003, p. 46-56.

Research output: Contribution to journalArticle

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title = "Organotin compounds bearing mesogenic sidechains: synthesis, x-ray structures and polymerisation chemistry",
abstract = "Organotin compounds R3Sn(CH2)(n+2)OC6H4C6H4Y (R-3 = Ph-3, Ph2Bu; Y = H, CN; n = 1-3) and RX2Sn(CH2)(n+2)OC6H4C6H4Y (R = Ph, Bu; Y = H, CN; X = Br, I; n = 1-3) have been synthesised and characterised by H-1-, C-13-, Sn-119-NMR and Mossbauer spectroscopies. X-ray crystallography reveals tetrahedral geometries for Ph3Sn(CH2)(4)OC6H4C6H5 and Ph3Sn(CH2)(3)OC6H4C6H4CN, a six-coordinated, bromine-bridged dimeric structure for PhBr2Sn(CH2)(3)OC6H4C6H5 containing a mer-Br3C2OSn coordination sphere about tin and a five-coordinated monomeric structure for PhBr2Sn(CH2)3OC6H4C6H4CN. In all cases there is strong alignment of mesogenic groups in the solid-state but only PhBr2Sn(CH2)(3)OC6H4C6H4CN shows any indication of liquid-crystal behaviour. Wurtz polymerisation of RBr2Sn(CH2)(5)OC6H4C6H5 (R = Ph, Bu), both of which contain non-chelating ether functions, generated polystannanes (RR'Sn)(n) with M-n 2.3 x 10(5); M-w 3.0 x 10(5); M-w/M-n 1.30 and M-n 1.3 x 10(5); M-w 2.5 x 10(5); M-w/M-n 1.96, respectively, while no polymer was obtained from chelated PhBr2Sn(CH2)(3)OC6H4C6H5 (C) 2003 Elsevier B.V. All rights reserved.",
author = "Deacon, {P R} and N Devylder and Hill, {M S} and Mahon, {M F} and Molloy, {K C} and Price, {G J}",
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T1 - Organotin compounds bearing mesogenic sidechains: synthesis, x-ray structures and polymerisation chemistry

AU - Deacon,P R

AU - Devylder,N

AU - Hill,M S

AU - Mahon,M F

AU - Molloy,K C

AU - Price,G J

N1 - ID number: ISI:000186691700007

PY - 2003

Y1 - 2003

N2 - Organotin compounds R3Sn(CH2)(n+2)OC6H4C6H4Y (R-3 = Ph-3, Ph2Bu; Y = H, CN; n = 1-3) and RX2Sn(CH2)(n+2)OC6H4C6H4Y (R = Ph, Bu; Y = H, CN; X = Br, I; n = 1-3) have been synthesised and characterised by H-1-, C-13-, Sn-119-NMR and Mossbauer spectroscopies. X-ray crystallography reveals tetrahedral geometries for Ph3Sn(CH2)(4)OC6H4C6H5 and Ph3Sn(CH2)(3)OC6H4C6H4CN, a six-coordinated, bromine-bridged dimeric structure for PhBr2Sn(CH2)(3)OC6H4C6H5 containing a mer-Br3C2OSn coordination sphere about tin and a five-coordinated monomeric structure for PhBr2Sn(CH2)3OC6H4C6H4CN. In all cases there is strong alignment of mesogenic groups in the solid-state but only PhBr2Sn(CH2)(3)OC6H4C6H4CN shows any indication of liquid-crystal behaviour. Wurtz polymerisation of RBr2Sn(CH2)(5)OC6H4C6H5 (R = Ph, Bu), both of which contain non-chelating ether functions, generated polystannanes (RR'Sn)(n) with M-n 2.3 x 10(5); M-w 3.0 x 10(5); M-w/M-n 1.30 and M-n 1.3 x 10(5); M-w 2.5 x 10(5); M-w/M-n 1.96, respectively, while no polymer was obtained from chelated PhBr2Sn(CH2)(3)OC6H4C6H5 (C) 2003 Elsevier B.V. All rights reserved.

AB - Organotin compounds R3Sn(CH2)(n+2)OC6H4C6H4Y (R-3 = Ph-3, Ph2Bu; Y = H, CN; n = 1-3) and RX2Sn(CH2)(n+2)OC6H4C6H4Y (R = Ph, Bu; Y = H, CN; X = Br, I; n = 1-3) have been synthesised and characterised by H-1-, C-13-, Sn-119-NMR and Mossbauer spectroscopies. X-ray crystallography reveals tetrahedral geometries for Ph3Sn(CH2)(4)OC6H4C6H5 and Ph3Sn(CH2)(3)OC6H4C6H4CN, a six-coordinated, bromine-bridged dimeric structure for PhBr2Sn(CH2)(3)OC6H4C6H5 containing a mer-Br3C2OSn coordination sphere about tin and a five-coordinated monomeric structure for PhBr2Sn(CH2)3OC6H4C6H4CN. In all cases there is strong alignment of mesogenic groups in the solid-state but only PhBr2Sn(CH2)(3)OC6H4C6H4CN shows any indication of liquid-crystal behaviour. Wurtz polymerisation of RBr2Sn(CH2)(5)OC6H4C6H5 (R = Ph, Bu), both of which contain non-chelating ether functions, generated polystannanes (RR'Sn)(n) with M-n 2.3 x 10(5); M-w 3.0 x 10(5); M-w/M-n 1.30 and M-n 1.3 x 10(5); M-w 2.5 x 10(5); M-w/M-n 1.96, respectively, while no polymer was obtained from chelated PhBr2Sn(CH2)(3)OC6H4C6H5 (C) 2003 Elsevier B.V. All rights reserved.

U2 - 10.1016/j.jorganchem.2003.08.003

DO - 10.1016/j.jorganchem.2003.08.003

M3 - Article

VL - 687

SP - 46

EP - 56

JO - Journal of Organometallic Chemistry

T2 - Journal of Organometallic Chemistry

JF - Journal of Organometallic Chemistry

SN - 0022-328X

IS - 1

ER -