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TTF - TetraThiaFulvalene (Read 5516 times)
Gerrit-Jan Linker
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TTF - TetraThiaFulvalene
03.09.09 at 10:14:20
 
TTF - TetraThiaFulvalene
 
     S                  S
  / \             / \
C       \       /       C
||       C = C       ||  
C       /       \       C
  \ /             \ /
     S                  S
   
(H2C2S2C)2
 
TTF+ salts are highly conducting due to:
  • π-π stacking of the planar TTF+ ions
    Precise stacking gives not the most interactions. When stacking is not perfect:
    • exchange interactions are less
    • octupole moments are repulsive

  • the high symmetry enhances delocalisation and with that it reduces Coulomb repulsion
  • the mild conditions to form the cation

Each ring has 7π electrons, 2 from each S and one from each C.
Oxidating TTF leads to a 6π electron configuration.
 
TTF was first synthesised in 1970.
 
TTFs serve as electron donors to obtain organic metals and organic superconductors.  
 
Bechgaard & Fabre salts:
A Bechgaard salt is any one of a number of organic charge-transfer complexes that exhibit superconductivity at low temperatures. All Bechgaard salts are formed using a small, planar organic molecule as an electron donor, with any of a number of electron acceptors.  
 
All Bechgaard salts have a variation on a single tetraselenafulvalene motiv. The Fabre sals have are based on tetrathiafulvalene.
See:
http://www.oraxcel.com/cgi-bin/yabb2/YaBB.pl?num=1253218602
 
Reference:
Wikipedia NL - Tetrathiafulvaleen
http://nl.wikipedia.org/wiki/Tetrathiafulvaleen
Bechgaard salt
http://en.wikipedia.org/wiki/Bechgaard_salt
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« Last Edit: 16.12.12 at 16:50:00 by Gerrit-Jan Linker »  

Gerrit-Jan Linker
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TTF derivatives
Reply #1 - 16.09.09 at 19:10:47
 
TTF derivatives
 

  • TMTTF: TetraMethylTetraThioFulvalene: C10S4H12  
     
         CH3      S       S       CH3
          \ / \ / \ /  
               ||       =       ||  
          / \ / \ / \
      CH3       S       S       CH3
     
    See also:  
    The crystal structure of (TMTTF)2ReO4, the chem. soc. of japan, 57, 2025 (1984), Kobayashi, Kobayashi, Sasaki, Saito, Inokuchi  
    http://www.journalarchive.jst.go.jp/jnlpdf.php?cdjournal=bcsj1926&cdvol=57&a mp;noissue=7&startpage=2025&lang=en&from=jnlabstract
     
  • TMTSF: tetramethyltetraselenafulvalene: C10Se4H12
     
      CH3      Se       Se       CH3
          \ / \      /      \ /
          ||       =       ||
          /      \ /      \      / \
      CH3      Se       Se       CH3  
     

     
    See also:
    The quasi-one dimensional Bechgaard salts (TMTSF)2X X = PF6, AsF6, etc
    (TMTSF)2PF6 at temperatures of about 1 K
    Crystal structure similar to (EDOTTF)2PF6
    http://www.pi1.uni-stuttgart.de/research/Elektronen/TMTSF_e.php
     
  • DT-TTF: dithiophenetetrathiafulvalene: C10S6H4
                S       S        
      // \ / \ / \ / \\
      S ||       =       ||      S
      \\ / \ / \ / \ //
                S       S      
     
    See also:
    Modelling organic molecular crystals by hybrid quantum mechanical/molecular mechanical embedding
    Chemical Physics Letters, Volume 457, Issues 1-3, 20 May 2008, Pages 154-158, Torras, Bromley, Betran, Illas
     
  • MDHT: C7S6H6
         S       S       S        
      / \ / \ / \
     /       || \ = |
     \       ||       / \       |
      \ / \ / \ /  
         S       S       S      
     
     
  • EDO-TTF:  
     
          O S       S  
      / \ / \ / \  
      | || = ||  
      \ / \ / \ /  
          O S       S  
     
  • MeEDO-TTF:
     
          O       S       S       CH3
      / \ / \ / \ /
      |       ||       =       ||  
      \ / \ / \ /  
          O       S       S  
     
  • EDHT:  
     
          S       S       S  
      / \ / \ / \  
      |       ||       =       |  
      \ / \ / \ /  
          S       S       S  
     
  • DODHT:  
     
      O       S       S       S  
     / \ / \ / \ / \  
    |       |       ||       =       |  
     \      / \ / \ / \ /  
      O       S       S       S  
     
    Not planar!  
    (DODHT)2PF6 is superconductor.
     
  • BEDO-TTF (BO):
     
         O       S       S       O
      / \ / \ / \ /      \
      |       ||       =       ||       |
      \ / \ / \ / \      /
         O       S       S       O
     
  • BEDT-TTF (ET):
     
         S       S       S       S
      / \ / \ / \ /      \
      |       ||       =       ||       |
      \ / \ / \ / \      /
         S       S       S       S
     
     
  • BEDT-TSF (BETS): BETS = bis(ethylenedithio)tetraselenafulvalene
     
         S      Se       Se       S
      / \ / \ / \ /      \
      |       ||       =       ||       |
      \ / \ / \ / \      /
         S       Se       Se       S
     
    See also:
    BETS as a source of molecular magnetic superconductors
    http://www.rsc.org/delivery/_ArticleLinking/DisplayArticleForFree.cfm?doi=b00209 5h&JournalCode=CS
     
  • BPDT-TTF (ET): BIS(PROPYLENEDITHIO)TETRATHIAFULVALENE
     
          _ S       S       S       _ S
      /      \ /      \ / \ /      \
      /       ||       =       ||       \
      \       ||       / \       ||       /
      \ _ / \ /      \ / \_      /
          S       S             S       S
     
    See also:
    CRYSTAL STRUCTURE OF THE SIMPLE RADICAL-CATION SALT (BPDT--TTF)HgBr 3
    http://www.springerlink.com/content/mh06v453x5210m0p/fulltext.pdf
     

 
Not a derivative but often mentioned as having similar properties: TCNQ:
 
  NC             C = C            CN
      \       /       \       /
      C = C             C = C
      /       \       /       \
  NC             C = C            CN
 
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« Last Edit: 26.09.09 at 09:02:03 by Gerrit-Jan Linker »  

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books about TTF
Reply #2 - 26.09.09 at 08:40:38
 
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TXF
Reply #3 - 17.09.11 at 22:01:08
 
TXF
 
TXF with X in {O,S,Se} = TOF (O), TTF (S), TSF (Se)
 
TOF - TetraOxaFulvalene
H4C6O4
 
TTF - TetraThiaFulvalene
H4C6S4
1,3-Dithiole, 2-(1,3-dithiol-2-ylidene)-;
Δ2,2'-Bi-1,3-dithiole; 1,4,5,8-Tetrathiafulvalene;  
δ-2:2'-bis(1,3-dithiazole)
 
TSF - TetraSelenaFulvalene
H4C6Se4
IUPAC: 2-(1,3-diselenol-2-ylidene)-1,3-diselenole
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« Last Edit: 18.09.11 at 22:16:26 by Gerrit-Jan Linker »  

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