Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone

Muhammad S. Khan, Muna R A Al-Mandhary, Mohammed K. Al-Suti, Birte Ahrens, Mary F. Mahon, Louise Male, Paul R. Raithby, Clare E. Boothby, Anna Köhler

Research output: Contribution to journalArticle

84 Citations (Scopus)

Abstract

A series of trimethylsilyl-protected and terminal mono- and bis-alkynes based on 9,9-dioctylfluorene, 2-(trimethylsilylethynyl)-9,9-dioctylfluorene la, 2-ethynyl-9,9-dioctylfluorene 1b, 2,7-bis(trimethylsilylethynyl)-9,9-dioctylfluorene 2a, 2,7-bis(ethynyl)-9,9-dioctylfluorene 2b, have been synthesised. Reaction of trans-[(PnBu3)2PtCl2] with 2 equivalents of the terminal ethyne 1b yields the mononuclear platinum(II) diyne 3, reaction of trans-[(Ph)(Et3P)2PtCl] with 0.5 equivalents of the diterminal ethyne 2b gives the dinuclear platinum(II) diyne 4 while 1 : 1 reaction between trans-[(PnBU3) 2PtCl2] and 2b gives the platinum(II) poly-yne 5. Treatment of 2,5-dioctyloxy-1,4-diiodobenzene with 1b in 1 : 2 stoichiometry produces the organic di-yne 6 while 1 : 1 reaction between 2,5-dioctyloxy-1,4-diiodobenzene and 2b, 2,7-bis(ethynyl)fluorene or 2,7-bis(ethynyl)fluoren-9-one produces the organic co-poly-ynes 7-9. All the new materials have been characterised by analytical and spectroscopic methods and the single crystal X-ray structures of 2a and 3 have been determined. The diynes and poly-ynes are soluble in organic solvents and are readily cast into thin films. Optical spectroscopic measurements reveal that the attachment of octyl side-chains on the fluorenyl spacer reduces inter-chain interaction in the poly-ynes while a fluorenonyl spacer creates a donor-acceptor interaction along the rigid backbone of the organometallic poly-ynes and organic co-poly-ynes.

Original languageEnglish
Pages (from-to)74-84
Number of pages11
JournalDalton Transactions
Issue number1
DOIs
Publication statusPublished - Jan 7 2003

Fingerprint

Fluorenes
Diynes
Platinum
Acetylene
Alkynes
Organometallics
Stoichiometry
Organic solvents
Single crystals
X rays
Thin films
Optical spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone. / Khan, Muhammad S.; Al-Mandhary, Muna R A; Al-Suti, Mohammed K.; Ahrens, Birte; Mahon, Mary F.; Male, Louise; Raithby, Paul R.; Boothby, Clare E.; Köhler, Anna.

In: Dalton Transactions, No. 1, 07.01.2003, p. 74-84.

Research output: Contribution to journalArticle

Khan, Muhammad S. ; Al-Mandhary, Muna R A ; Al-Suti, Mohammed K. ; Ahrens, Birte ; Mahon, Mary F. ; Male, Louise ; Raithby, Paul R. ; Boothby, Clare E. ; Köhler, Anna. / Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone. In: Dalton Transactions. 2003 ; No. 1. pp. 74-84.
@article{2a57af59137f4295a6203860fad1a9d6,
title = "Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone",
abstract = "A series of trimethylsilyl-protected and terminal mono- and bis-alkynes based on 9,9-dioctylfluorene, 2-(trimethylsilylethynyl)-9,9-dioctylfluorene la, 2-ethynyl-9,9-dioctylfluorene 1b, 2,7-bis(trimethylsilylethynyl)-9,9-dioctylfluorene 2a, 2,7-bis(ethynyl)-9,9-dioctylfluorene 2b, have been synthesised. Reaction of trans-[(PnBu3)2PtCl2] with 2 equivalents of the terminal ethyne 1b yields the mononuclear platinum(II) diyne 3, reaction of trans-[(Ph)(Et3P)2PtCl] with 0.5 equivalents of the diterminal ethyne 2b gives the dinuclear platinum(II) diyne 4 while 1 : 1 reaction between trans-[(PnBU3) 2PtCl2] and 2b gives the platinum(II) poly-yne 5. Treatment of 2,5-dioctyloxy-1,4-diiodobenzene with 1b in 1 : 2 stoichiometry produces the organic di-yne 6 while 1 : 1 reaction between 2,5-dioctyloxy-1,4-diiodobenzene and 2b, 2,7-bis(ethynyl)fluorene or 2,7-bis(ethynyl)fluoren-9-one produces the organic co-poly-ynes 7-9. All the new materials have been characterised by analytical and spectroscopic methods and the single crystal X-ray structures of 2a and 3 have been determined. The diynes and poly-ynes are soluble in organic solvents and are readily cast into thin films. Optical spectroscopic measurements reveal that the attachment of octyl side-chains on the fluorenyl spacer reduces inter-chain interaction in the poly-ynes while a fluorenonyl spacer creates a donor-acceptor interaction along the rigid backbone of the organometallic poly-ynes and organic co-poly-ynes.",
author = "Khan, {Muhammad S.} and Al-Mandhary, {Muna R A} and Al-Suti, {Mohammed K.} and Birte Ahrens and Mahon, {Mary F.} and Louise Male and Raithby, {Paul R.} and Boothby, {Clare E.} and Anna K{\"o}hler",
year = "2003",
month = "1",
day = "7",
doi = "10.1039/b208963g",
language = "English",
pages = "74--84",
journal = "Dalton Transactions",
issn = "1477-9226",
publisher = "Royal Society of Chemistry",
number = "1",

}

TY - JOUR

T1 - Synthesis, characterisation and optical spectroscopy of diynes and poly-ynes containing derivatised fluorenes in the backbone

AU - Khan, Muhammad S.

AU - Al-Mandhary, Muna R A

AU - Al-Suti, Mohammed K.

AU - Ahrens, Birte

AU - Mahon, Mary F.

AU - Male, Louise

AU - Raithby, Paul R.

AU - Boothby, Clare E.

AU - Köhler, Anna

PY - 2003/1/7

Y1 - 2003/1/7

N2 - A series of trimethylsilyl-protected and terminal mono- and bis-alkynes based on 9,9-dioctylfluorene, 2-(trimethylsilylethynyl)-9,9-dioctylfluorene la, 2-ethynyl-9,9-dioctylfluorene 1b, 2,7-bis(trimethylsilylethynyl)-9,9-dioctylfluorene 2a, 2,7-bis(ethynyl)-9,9-dioctylfluorene 2b, have been synthesised. Reaction of trans-[(PnBu3)2PtCl2] with 2 equivalents of the terminal ethyne 1b yields the mononuclear platinum(II) diyne 3, reaction of trans-[(Ph)(Et3P)2PtCl] with 0.5 equivalents of the diterminal ethyne 2b gives the dinuclear platinum(II) diyne 4 while 1 : 1 reaction between trans-[(PnBU3) 2PtCl2] and 2b gives the platinum(II) poly-yne 5. Treatment of 2,5-dioctyloxy-1,4-diiodobenzene with 1b in 1 : 2 stoichiometry produces the organic di-yne 6 while 1 : 1 reaction between 2,5-dioctyloxy-1,4-diiodobenzene and 2b, 2,7-bis(ethynyl)fluorene or 2,7-bis(ethynyl)fluoren-9-one produces the organic co-poly-ynes 7-9. All the new materials have been characterised by analytical and spectroscopic methods and the single crystal X-ray structures of 2a and 3 have been determined. The diynes and poly-ynes are soluble in organic solvents and are readily cast into thin films. Optical spectroscopic measurements reveal that the attachment of octyl side-chains on the fluorenyl spacer reduces inter-chain interaction in the poly-ynes while a fluorenonyl spacer creates a donor-acceptor interaction along the rigid backbone of the organometallic poly-ynes and organic co-poly-ynes.

AB - A series of trimethylsilyl-protected and terminal mono- and bis-alkynes based on 9,9-dioctylfluorene, 2-(trimethylsilylethynyl)-9,9-dioctylfluorene la, 2-ethynyl-9,9-dioctylfluorene 1b, 2,7-bis(trimethylsilylethynyl)-9,9-dioctylfluorene 2a, 2,7-bis(ethynyl)-9,9-dioctylfluorene 2b, have been synthesised. Reaction of trans-[(PnBu3)2PtCl2] with 2 equivalents of the terminal ethyne 1b yields the mononuclear platinum(II) diyne 3, reaction of trans-[(Ph)(Et3P)2PtCl] with 0.5 equivalents of the diterminal ethyne 2b gives the dinuclear platinum(II) diyne 4 while 1 : 1 reaction between trans-[(PnBU3) 2PtCl2] and 2b gives the platinum(II) poly-yne 5. Treatment of 2,5-dioctyloxy-1,4-diiodobenzene with 1b in 1 : 2 stoichiometry produces the organic di-yne 6 while 1 : 1 reaction between 2,5-dioctyloxy-1,4-diiodobenzene and 2b, 2,7-bis(ethynyl)fluorene or 2,7-bis(ethynyl)fluoren-9-one produces the organic co-poly-ynes 7-9. All the new materials have been characterised by analytical and spectroscopic methods and the single crystal X-ray structures of 2a and 3 have been determined. The diynes and poly-ynes are soluble in organic solvents and are readily cast into thin films. Optical spectroscopic measurements reveal that the attachment of octyl side-chains on the fluorenyl spacer reduces inter-chain interaction in the poly-ynes while a fluorenonyl spacer creates a donor-acceptor interaction along the rigid backbone of the organometallic poly-ynes and organic co-poly-ynes.

UR - http://www.scopus.com/inward/record.url?scp=18444402587&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=18444402587&partnerID=8YFLogxK

U2 - 10.1039/b208963g

DO - 10.1039/b208963g

M3 - Article

SP - 74

EP - 84

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

IS - 1

ER -