Synthesis, characterisation and optical spectroscopy of platinum(II) di-ynes and poly-ynes incorporating condensed aromatic spacers in the backbone

M S Khan, M R A Al-Mandhary, M K Al-Suti, F R Al-Battashi, S Al-Saadi, B Ahrens, J K Bjernemose, M F Mahon, P R Raithby, M Younus, N Chawdhury, A Kohler, E A Marseglia, E Tedesco, N Feeder, S J Teat

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Abstract

A series of protected and terminal dialkynes with extended.-conjugation through a condensed aromatic linker unit in the backbone, 1,4-bis(trimethylsilylethynyl) naphthalene, 2a, 1,4-bis(ethynyl)naphthalene, 2b, 9,10-bis(trimethylsilylethynyl)anthracene 3a, 9,10-bis(ethynyl)anthracene 3b, have been synthesized and characterized spectroscopically. The solid-state structures of 2a and 3a have been confirmed by single crystal X-ray diffraction studies. Reaction of two equivalents of the complex trans-[Ph(Et3P)(2)PtCl] with an equivalent of the terminal dialkynes 1,4-bis(ethynyl) benzene 1b and 2b-3b, in (Pr2NH)-Pr-i-CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-ynes trans-[Ph(Et3P)(2)Pt-C=C-R-C=C-Pt(PEt3)(2)Ph] (R = benzene-1,4-diyl 1c; naphthalene-1,4-diyl 2c and anthracene-9,10-diyl 3c) while reactions between equimolar quantities of trans-[((Bu3P)-Bu-n)(2)PtCl2] and 2b-3b under similar conditions readily afforded the platinum(II) poly-ynes trans-[-((Bu3P)-Bu-n)(2)Pt-C=C-R-C=C-](n) (R= naphthalene-1,4-diyl 2d and anthracene-9,10-diyl 3d). The Pt(II) diynes and poly-ynes have been characterized by analytical and spectroscopic methods, and the single crystal X-ray structures of 1c and 2c have been determined. These structures confirm the trans- square planar geometry at the platinum centres and the linear nature of the molecules. The di-ynes and poly-ynes are soluble in organic solvents and readily cast into thin films. Optical spectroscopic measurements reveal that the electron-rich naphthalene and anthracene spacers create strong donor - acceptor interactions between the Pt(II) centres and conjugated ligands along the rigid backbone of the organometallic polymers. Thermogravimetry shows that the di-ynes possess a somewhat higher thermal stability than the corresponding poly-ynes. Both the Pt(II) di-ynes and the poly-ynes exhibit increasing thermal stability along the series of spacers from phenylene through naphthalene to anthracene.
Original languageEnglish
Pages (from-to)2377-2385
Number of pages9
JournalDalton Transactions
Issue number15
DOIs
Publication statusPublished - 2004

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Platinum
Benzene
Diynes
Thermodynamic stability
Single crystals
Organometallics
Organic solvents
Thermogravimetric analysis
Optical spectroscopy
anthracene
naphthalene
Polymers
Ligands
X ray diffraction
X rays
Thin films
Molecules
Geometry
Electrons
Temperature

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Khan, M. S., Al-Mandhary, M. R. A., Al-Suti, M. K., Al-Battashi, F. R., Al-Saadi, S., Ahrens, B., ... Teat, S. J. (2004). Synthesis, characterisation and optical spectroscopy of platinum(II) di-ynes and poly-ynes incorporating condensed aromatic spacers in the backbone. Dalton Transactions, (15), 2377-2385. https://doi.org/10.1039/b405070c

Synthesis, characterisation and optical spectroscopy of platinum(II) di-ynes and poly-ynes incorporating condensed aromatic spacers in the backbone. / Khan, M S; Al-Mandhary, M R A; Al-Suti, M K; Al-Battashi, F R; Al-Saadi, S; Ahrens, B; Bjernemose, J K; Mahon, M F; Raithby, P R; Younus, M; Chawdhury, N; Kohler, A; Marseglia, E A; Tedesco, E; Feeder, N; Teat, S J.

In: Dalton Transactions, No. 15, 2004, p. 2377-2385.

Research output: Contribution to journalArticle

Khan, MS, Al-Mandhary, MRA, Al-Suti, MK, Al-Battashi, FR, Al-Saadi, S, Ahrens, B, Bjernemose, JK, Mahon, MF, Raithby, PR, Younus, M, Chawdhury, N, Kohler, A, Marseglia, EA, Tedesco, E, Feeder, N & Teat, SJ 2004, 'Synthesis, characterisation and optical spectroscopy of platinum(II) di-ynes and poly-ynes incorporating condensed aromatic spacers in the backbone', Dalton Transactions, no. 15, pp. 2377-2385. https://doi.org/10.1039/b405070c
Khan, M S ; Al-Mandhary, M R A ; Al-Suti, M K ; Al-Battashi, F R ; Al-Saadi, S ; Ahrens, B ; Bjernemose, J K ; Mahon, M F ; Raithby, P R ; Younus, M ; Chawdhury, N ; Kohler, A ; Marseglia, E A ; Tedesco, E ; Feeder, N ; Teat, S J. / Synthesis, characterisation and optical spectroscopy of platinum(II) di-ynes and poly-ynes incorporating condensed aromatic spacers in the backbone. In: Dalton Transactions. 2004 ; No. 15. pp. 2377-2385.
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abstract = "A series of protected and terminal dialkynes with extended.-conjugation through a condensed aromatic linker unit in the backbone, 1,4-bis(trimethylsilylethynyl) naphthalene, 2a, 1,4-bis(ethynyl)naphthalene, 2b, 9,10-bis(trimethylsilylethynyl)anthracene 3a, 9,10-bis(ethynyl)anthracene 3b, have been synthesized and characterized spectroscopically. The solid-state structures of 2a and 3a have been confirmed by single crystal X-ray diffraction studies. Reaction of two equivalents of the complex trans-[Ph(Et3P)(2)PtCl] with an equivalent of the terminal dialkynes 1,4-bis(ethynyl) benzene 1b and 2b-3b, in (Pr2NH)-Pr-i-CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-ynes trans-[Ph(Et3P)(2)Pt-C=C-R-C=C-Pt(PEt3)(2)Ph] (R = benzene-1,4-diyl 1c; naphthalene-1,4-diyl 2c and anthracene-9,10-diyl 3c) while reactions between equimolar quantities of trans-[((Bu3P)-Bu-n)(2)PtCl2] and 2b-3b under similar conditions readily afforded the platinum(II) poly-ynes trans-[-((Bu3P)-Bu-n)(2)Pt-C=C-R-C=C-](n) (R= naphthalene-1,4-diyl 2d and anthracene-9,10-diyl 3d). The Pt(II) diynes and poly-ynes have been characterized by analytical and spectroscopic methods, and the single crystal X-ray structures of 1c and 2c have been determined. These structures confirm the trans- square planar geometry at the platinum centres and the linear nature of the molecules. The di-ynes and poly-ynes are soluble in organic solvents and readily cast into thin films. Optical spectroscopic measurements reveal that the electron-rich naphthalene and anthracene spacers create strong donor - acceptor interactions between the Pt(II) centres and conjugated ligands along the rigid backbone of the organometallic polymers. Thermogravimetry shows that the di-ynes possess a somewhat higher thermal stability than the corresponding poly-ynes. Both the Pt(II) di-ynes and the poly-ynes exhibit increasing thermal stability along the series of spacers from phenylene through naphthalene to anthracene.",
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T1 - Synthesis, characterisation and optical spectroscopy of platinum(II) di-ynes and poly-ynes incorporating condensed aromatic spacers in the backbone

AU - Khan, M S

AU - Al-Mandhary, M R A

AU - Al-Suti, M K

AU - Al-Battashi, F R

AU - Al-Saadi, S

AU - Ahrens, B

AU - Bjernemose, J K

AU - Mahon, M F

AU - Raithby, P R

AU - Younus, M

AU - Chawdhury, N

AU - Kohler, A

AU - Marseglia, E A

AU - Tedesco, E

AU - Feeder, N

AU - Teat, S J

N1 - ID number: ISI:000222909800026

PY - 2004

Y1 - 2004

N2 - A series of protected and terminal dialkynes with extended.-conjugation through a condensed aromatic linker unit in the backbone, 1,4-bis(trimethylsilylethynyl) naphthalene, 2a, 1,4-bis(ethynyl)naphthalene, 2b, 9,10-bis(trimethylsilylethynyl)anthracene 3a, 9,10-bis(ethynyl)anthracene 3b, have been synthesized and characterized spectroscopically. The solid-state structures of 2a and 3a have been confirmed by single crystal X-ray diffraction studies. Reaction of two equivalents of the complex trans-[Ph(Et3P)(2)PtCl] with an equivalent of the terminal dialkynes 1,4-bis(ethynyl) benzene 1b and 2b-3b, in (Pr2NH)-Pr-i-CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-ynes trans-[Ph(Et3P)(2)Pt-C=C-R-C=C-Pt(PEt3)(2)Ph] (R = benzene-1,4-diyl 1c; naphthalene-1,4-diyl 2c and anthracene-9,10-diyl 3c) while reactions between equimolar quantities of trans-[((Bu3P)-Bu-n)(2)PtCl2] and 2b-3b under similar conditions readily afforded the platinum(II) poly-ynes trans-[-((Bu3P)-Bu-n)(2)Pt-C=C-R-C=C-](n) (R= naphthalene-1,4-diyl 2d and anthracene-9,10-diyl 3d). The Pt(II) diynes and poly-ynes have been characterized by analytical and spectroscopic methods, and the single crystal X-ray structures of 1c and 2c have been determined. These structures confirm the trans- square planar geometry at the platinum centres and the linear nature of the molecules. The di-ynes and poly-ynes are soluble in organic solvents and readily cast into thin films. Optical spectroscopic measurements reveal that the electron-rich naphthalene and anthracene spacers create strong donor - acceptor interactions between the Pt(II) centres and conjugated ligands along the rigid backbone of the organometallic polymers. Thermogravimetry shows that the di-ynes possess a somewhat higher thermal stability than the corresponding poly-ynes. Both the Pt(II) di-ynes and the poly-ynes exhibit increasing thermal stability along the series of spacers from phenylene through naphthalene to anthracene.

AB - A series of protected and terminal dialkynes with extended.-conjugation through a condensed aromatic linker unit in the backbone, 1,4-bis(trimethylsilylethynyl) naphthalene, 2a, 1,4-bis(ethynyl)naphthalene, 2b, 9,10-bis(trimethylsilylethynyl)anthracene 3a, 9,10-bis(ethynyl)anthracene 3b, have been synthesized and characterized spectroscopically. The solid-state structures of 2a and 3a have been confirmed by single crystal X-ray diffraction studies. Reaction of two equivalents of the complex trans-[Ph(Et3P)(2)PtCl] with an equivalent of the terminal dialkynes 1,4-bis(ethynyl) benzene 1b and 2b-3b, in (Pr2NH)-Pr-i-CH2Cl2, in the presence of CuI, at room temperature, afforded the platinum(II) di-ynes trans-[Ph(Et3P)(2)Pt-C=C-R-C=C-Pt(PEt3)(2)Ph] (R = benzene-1,4-diyl 1c; naphthalene-1,4-diyl 2c and anthracene-9,10-diyl 3c) while reactions between equimolar quantities of trans-[((Bu3P)-Bu-n)(2)PtCl2] and 2b-3b under similar conditions readily afforded the platinum(II) poly-ynes trans-[-((Bu3P)-Bu-n)(2)Pt-C=C-R-C=C-](n) (R= naphthalene-1,4-diyl 2d and anthracene-9,10-diyl 3d). The Pt(II) diynes and poly-ynes have been characterized by analytical and spectroscopic methods, and the single crystal X-ray structures of 1c and 2c have been determined. These structures confirm the trans- square planar geometry at the platinum centres and the linear nature of the molecules. The di-ynes and poly-ynes are soluble in organic solvents and readily cast into thin films. Optical spectroscopic measurements reveal that the electron-rich naphthalene and anthracene spacers create strong donor - acceptor interactions between the Pt(II) centres and conjugated ligands along the rigid backbone of the organometallic polymers. Thermogravimetry shows that the di-ynes possess a somewhat higher thermal stability than the corresponding poly-ynes. Both the Pt(II) di-ynes and the poly-ynes exhibit increasing thermal stability along the series of spacers from phenylene through naphthalene to anthracene.

U2 - 10.1039/b405070c

DO - 10.1039/b405070c

M3 - Article

SP - 2377

EP - 2385

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 15

ER -