Synthesis and characterisation of new acetylide-functionalised aromatic and hetero-aromatic ligands and their dinuclear platinum complexes

M S Khan, M K Al-Suti, M R A Al-Mandhary, B Ahrens, J K Bjernemose, M F Mahon, L Male, P R Raithby, R H Friend, A Kohler, J S Wilson

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Abstract

A new series of rigid rod protected and terminal dialkynes with extended pi-conjugation through aromatic and hetero-aromatic linker units in the backbone, 2,5-bis(trimethylsilylethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1a, 2,5-bis(ethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1b, 5,8- bis( trimethylsilylethynyl) quinoline 2a, 5,8-bis( ethynyl) quinoline 2b, 2,3-diphenyl-5,8-bis(trimethylsilylethynyl) quinoxaline 3a, 2,3-diphenyl-5,8-bis( ethynyl) quinoxaline 3b, 4,7-bis(trimethysilylethynyl)-2,1,3-benzothiadiazole 4a and 4,7-bis( ethynyl)-2,1,3-benzothiadiazole 4b, has been synthesised. Treatment of the complex trans-[Pt(Ph)(Cl)(Et3P)(2)] with half an equivalent of the diterminal alkynes 1b-4b in (Pr2NH)-Pr-i-CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-yne complexes trans-[(Et3P)(2) (Ph) Pt-C=C-R-C=C-Pt(Ph)(Et3P)(2)] [R = 1-(2-ethylhexyloxy)-4-methoxybenzene- 2,5-diyl 1c, quninoline-5,8-diyl 2c, 2,3-diphenylquinoxaline-5,8-diyl 3c, 2,1,3-benzothiadiazole- 4,7-diyl 4c] in good yields. The new acetylide-functionalised ligands and the platinum(II) sigma-acetylide complexes have been characterised by analytical and spectroscopic methods and X-ray single crystal structure determinations for 2c-4c. The absorption spectra of the complexes 2c-4c show substantial donor-acceptor interaction between the platinum(II) centres and the conjugated ligands. The photoluminescence spectra of 1c-3c show characteristic singlet (S-1) and triplet (T-1) emissions. Both the singlet and triplet emissions as well as the absorption decrease in energy with increasing electronegativity of the spacer groups along the series 1c-4c.
Original languageEnglish
Pages (from-to)65-73
Number of pages9
JournalDalton Transactions
Issue number1
DOIs
Publication statusPublished - 2003

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Platinum
Quinoxalines
Ligands
Electronegativity
Alkynes
Absorption spectra
Photoluminescence
Crystal structure
Single crystals
X rays
benzo-1,2,3-thiadiazole
anisole
Temperature
diphenyl
quinoline

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Synthesis and characterisation of new acetylide-functionalised aromatic and hetero-aromatic ligands and their dinuclear platinum complexes. / Khan, M S; Al-Suti, M K; Al-Mandhary, M R A; Ahrens, B; Bjernemose, J K; Mahon, M F; Male, L; Raithby, P R; Friend, R H; Kohler, A; Wilson, J S.

In: Dalton Transactions, No. 1, 2003, p. 65-73.

Research output: Contribution to journalArticle

Khan, MS, Al-Suti, MK, Al-Mandhary, MRA, Ahrens, B, Bjernemose, JK, Mahon, MF, Male, L, Raithby, PR, Friend, RH, Kohler, A & Wilson, JS 2003, 'Synthesis and characterisation of new acetylide-functionalised aromatic and hetero-aromatic ligands and their dinuclear platinum complexes', Dalton Transactions, no. 1, pp. 65-73. https://doi.org/10.1039/b208494e
Khan, M S ; Al-Suti, M K ; Al-Mandhary, M R A ; Ahrens, B ; Bjernemose, J K ; Mahon, M F ; Male, L ; Raithby, P R ; Friend, R H ; Kohler, A ; Wilson, J S. / Synthesis and characterisation of new acetylide-functionalised aromatic and hetero-aromatic ligands and their dinuclear platinum complexes. In: Dalton Transactions. 2003 ; No. 1. pp. 65-73.
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title = "Synthesis and characterisation of new acetylide-functionalised aromatic and hetero-aromatic ligands and their dinuclear platinum complexes",
abstract = "A new series of rigid rod protected and terminal dialkynes with extended pi-conjugation through aromatic and hetero-aromatic linker units in the backbone, 2,5-bis(trimethylsilylethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1a, 2,5-bis(ethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1b, 5,8- bis( trimethylsilylethynyl) quinoline 2a, 5,8-bis( ethynyl) quinoline 2b, 2,3-diphenyl-5,8-bis(trimethylsilylethynyl) quinoxaline 3a, 2,3-diphenyl-5,8-bis( ethynyl) quinoxaline 3b, 4,7-bis(trimethysilylethynyl)-2,1,3-benzothiadiazole 4a and 4,7-bis( ethynyl)-2,1,3-benzothiadiazole 4b, has been synthesised. Treatment of the complex trans-[Pt(Ph)(Cl)(Et3P)(2)] with half an equivalent of the diterminal alkynes 1b-4b in (Pr2NH)-Pr-i-CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-yne complexes trans-[(Et3P)(2) (Ph) Pt-C=C-R-C=C-Pt(Ph)(Et3P)(2)] [R = 1-(2-ethylhexyloxy)-4-methoxybenzene- 2,5-diyl 1c, quninoline-5,8-diyl 2c, 2,3-diphenylquinoxaline-5,8-diyl 3c, 2,1,3-benzothiadiazole- 4,7-diyl 4c] in good yields. The new acetylide-functionalised ligands and the platinum(II) sigma-acetylide complexes have been characterised by analytical and spectroscopic methods and X-ray single crystal structure determinations for 2c-4c. The absorption spectra of the complexes 2c-4c show substantial donor-acceptor interaction between the platinum(II) centres and the conjugated ligands. The photoluminescence spectra of 1c-3c show characteristic singlet (S-1) and triplet (T-1) emissions. Both the singlet and triplet emissions as well as the absorption decrease in energy with increasing electronegativity of the spacer groups along the series 1c-4c.",
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T1 - Synthesis and characterisation of new acetylide-functionalised aromatic and hetero-aromatic ligands and their dinuclear platinum complexes

AU - Khan, M S

AU - Al-Suti, M K

AU - Al-Mandhary, M R A

AU - Ahrens, B

AU - Bjernemose, J K

AU - Mahon, M F

AU - Male, L

AU - Raithby, P R

AU - Friend, R H

AU - Kohler, A

AU - Wilson, J S

N1 - ID number: ISI:000181292000010

PY - 2003

Y1 - 2003

N2 - A new series of rigid rod protected and terminal dialkynes with extended pi-conjugation through aromatic and hetero-aromatic linker units in the backbone, 2,5-bis(trimethylsilylethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1a, 2,5-bis(ethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1b, 5,8- bis( trimethylsilylethynyl) quinoline 2a, 5,8-bis( ethynyl) quinoline 2b, 2,3-diphenyl-5,8-bis(trimethylsilylethynyl) quinoxaline 3a, 2,3-diphenyl-5,8-bis( ethynyl) quinoxaline 3b, 4,7-bis(trimethysilylethynyl)-2,1,3-benzothiadiazole 4a and 4,7-bis( ethynyl)-2,1,3-benzothiadiazole 4b, has been synthesised. Treatment of the complex trans-[Pt(Ph)(Cl)(Et3P)(2)] with half an equivalent of the diterminal alkynes 1b-4b in (Pr2NH)-Pr-i-CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-yne complexes trans-[(Et3P)(2) (Ph) Pt-C=C-R-C=C-Pt(Ph)(Et3P)(2)] [R = 1-(2-ethylhexyloxy)-4-methoxybenzene- 2,5-diyl 1c, quninoline-5,8-diyl 2c, 2,3-diphenylquinoxaline-5,8-diyl 3c, 2,1,3-benzothiadiazole- 4,7-diyl 4c] in good yields. The new acetylide-functionalised ligands and the platinum(II) sigma-acetylide complexes have been characterised by analytical and spectroscopic methods and X-ray single crystal structure determinations for 2c-4c. The absorption spectra of the complexes 2c-4c show substantial donor-acceptor interaction between the platinum(II) centres and the conjugated ligands. The photoluminescence spectra of 1c-3c show characteristic singlet (S-1) and triplet (T-1) emissions. Both the singlet and triplet emissions as well as the absorption decrease in energy with increasing electronegativity of the spacer groups along the series 1c-4c.

AB - A new series of rigid rod protected and terminal dialkynes with extended pi-conjugation through aromatic and hetero-aromatic linker units in the backbone, 2,5-bis(trimethylsilylethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1a, 2,5-bis(ethynyl)-1-(2-ethylhexyloxy)-4-methoxybenzene 1b, 5,8- bis( trimethylsilylethynyl) quinoline 2a, 5,8-bis( ethynyl) quinoline 2b, 2,3-diphenyl-5,8-bis(trimethylsilylethynyl) quinoxaline 3a, 2,3-diphenyl-5,8-bis( ethynyl) quinoxaline 3b, 4,7-bis(trimethysilylethynyl)-2,1,3-benzothiadiazole 4a and 4,7-bis( ethynyl)-2,1,3-benzothiadiazole 4b, has been synthesised. Treatment of the complex trans-[Pt(Ph)(Cl)(Et3P)(2)] with half an equivalent of the diterminal alkynes 1b-4b in (Pr2NH)-Pr-i-CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-yne complexes trans-[(Et3P)(2) (Ph) Pt-C=C-R-C=C-Pt(Ph)(Et3P)(2)] [R = 1-(2-ethylhexyloxy)-4-methoxybenzene- 2,5-diyl 1c, quninoline-5,8-diyl 2c, 2,3-diphenylquinoxaline-5,8-diyl 3c, 2,1,3-benzothiadiazole- 4,7-diyl 4c] in good yields. The new acetylide-functionalised ligands and the platinum(II) sigma-acetylide complexes have been characterised by analytical and spectroscopic methods and X-ray single crystal structure determinations for 2c-4c. The absorption spectra of the complexes 2c-4c show substantial donor-acceptor interaction between the platinum(II) centres and the conjugated ligands. The photoluminescence spectra of 1c-3c show characteristic singlet (S-1) and triplet (T-1) emissions. Both the singlet and triplet emissions as well as the absorption decrease in energy with increasing electronegativity of the spacer groups along the series 1c-4c.

U2 - 10.1039/b208494e

DO - 10.1039/b208494e

M3 - Article

SP - 65

EP - 73

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 1

ER -