snythesis of polymers [kompatibilitätsmodus] · introduction and synthesis of...
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LINZ LECTURES
Lecture 1. The Development of Organic Conductors: M t l S d t d S i d tMetals, Superconductors and Semiconductors
Lecture 2A Introduction and Synthesis of ImportantLecture 2A. Introduction and Synthesis of Important Conjugated Polymers
Lecture 2B. Solid State Polymerization
Lecture 3 Fullerene ChemistryLecture 3. Fullerene Chemistry
Lecture 3B. Molecular Engineeringg g
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Introduction and Synthesis of Important Conjugated Polymers
Linz, June 10, 2008
General Introduction
Solution PolymerizationSolution Polymerization
OligolyacenesOligolyacenes
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Types of Polymers
A A A A A A A A H l-A-A.A-A.A-A-A-A- Homopolymer
-A-B-B-A-B-A-A-B- Random copolymerA B B A B A A B Random copolymer
-A-B-A-B-A-B-A-B- Alternating copolymer
-A-A-A-A-B-B-B-B- Block copolymer
-A-A-A-A-A-A-A-A Graft copolymer||B-B-B-B-B-B
Malcolm P. Stevens “Polymer Chemistry: an Introduction” 3rd Ed. Oxford, 1999
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Types of Chains
(a) Linear chain, (b) branched chain, (c) network
Malcolm P. Stevens “Polymer Chemistry: an Introduction” 3rd Ed. Oxford, 1999
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Types of Architectures
(h)
(a) Star (b) comb (c) ladder (d) pseudo ladder (e) rotaxane (f) catenane (g) dendrimer (h)
(h)
Malcolm P. Stevens “Polymer Chemistry: an Introduction” 3rd Ed. Oxford, 1999
(a) Star, (b) comb, (c) ladder, (d) pseudo ladder, (e) rotaxane, (f) catenane, (g) dendrimer (h) rigid rod
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Malcolm P. Stevens “Polymer Chemistry: an Introduction” 3rd Ed. Oxford, 1999
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“For drawn samples, values for the Young's modulus as high as 37 GPa and tensile strength up to 500 MPa have been measured in the machine direction. g pThese properties approach those of many high performance fibers.”
Machado J M ; Masse M A ; Karasz F E Polymer 1989 30 1992Machado, J.M.; Masse, M.A.; Karasz, F.E. Polymer, 1989, 30, 1992
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Step Growth or Condensation Polymerization
O O O O
H2N(CH2)6NH2 Cl (CH2)4 Cl HN(H2C)6-HN (CH2)4 n
+
A B -(A-B)-n
Nylon 66
O
H2N(CH2)5 CO2H HN(H2C)5-n
A -(A-)n
M l K l K t PPT PT PP
Nylon 6
Mylar, Kevlar, Kapton, PPT, PT, PPy
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Carothers Equation
Malcolm P. Stevens “Polymer Chemistry: an Introduction” 3rd Ed. Oxford, 1999
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Chain Growth or Addition Polymerization
Free Radical
Ph OO Ph
O
NN
CNCN
Initiator RΔor hν
RG G
Initiators:Thermal
O O
Ph O
OR H2C CH R CH2CH
R CH2CHG
H2C CHG
R CH2CHG
CH2CHG
+
+
PhPh
O
OH
PhPh
O
RS-SR
Photochemical
R CH2CHG
CH2CHG
H2C CHG
[CH2CH(G)]n
Photochemical
R + HC CH Intractable products
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Chain-Growth Polymerization
Malcolm P. Stevens “Polymer Chemistry: an Introduction” 3rd Ed. Oxford, 1999
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Ziegler-Natta Polymerization
H2C CHG
Z-N[CH2CH(G)]n2 [ 2 ( )]n
Z-N: Ti(OR)4 AlR3
Z-NHC CH
Z N[CH=CH]n
Anionic, LivingCationic,
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Ring Opening Metathesis Polymerization (ROMP)
LnRu=CHPh-(CH=CH)n
R
LnRu=CHPh-(CH=CH-CH=CH-CH=CH-CH=CR)n
R
QuickTime™ and aTIFF (Uncompressed) decompressor
are needed to see this picture.LnRu=CHPh =
Scherman O. A; Rutenberg I. M; Grubbs R. H J. Am. Chem. Soc. 2003, 125, 8515
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Organometallic Methods:
Br-Ar-Br (Ar)nCat
Kumada, Yamamoto, Colon
Cat: PdL4, NiL2
Suzuki
Br-Ar-Br (RO)2BAr'-B(OR)2 (Ar-Ar')nCat
+
HeckHeck
Br-Ar-Br Ar' Ar' Arn
Cat
R R
GRIM/Kumada
n
X BrBrGRIMCat
X S
X n
X = S
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Sheina, E.E.; Iovu, M.C.; McCullough, R.D. Polym. Prepr. 2005, 46(1), 682
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Oxidative (Cationic) Polymerization
R
FeIII
R R
XH
-2H
R
X
X
Fe
X2 2
X
RH
R
2H
R R R
X
X
R
-e(-)
X
R
X FeIII
X
R
X
X
R
X X
X
R
-e(-)
R RR R R R
R R
X
X
R
X
R
X-2H
X
X X
R
XFeIII
X = S, N
R R R R
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Oxidative Polymerization
RR RR
Thiophene as a “handle”
X
R
ArX
R
FeIII
X
R
ArX
R
nXX XX n
Polyaniline
NH2
-e(-)
(NH4)2S2O8
NH
x
Ny
e x N
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Reductive (Anionic) Polymerization
BrBr O
O Hg( )
O
O
O +e(-)
nBr Br
Utley, J.H.; Gao, Y.; Gruber, J.; Zhang, Y.; Munoz-Escalona, A. Chem Mater. 1995, 5, 1837
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Reductive Polymerization
BrBr O
O
O
Hg
+e(-)
O
Br Brn
B B BBr Br
O Hg( )
O
OBr
O
O
O
O
BrHg
BrBr
O +e(-)
nBr
O
nBr
+e(-)
Utley, J.H.; Gao, Y.; Gruber, J.; Zhang, Y.; Munoz-Escalona, A. Chem Mater. 1995, 5, 1837
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PPV Synthesis
SMe2SMe2 SMe2
*
Me2S*
*
* = (-) or (•)
SMe2
Δ+ (CH3)2S
( ) or ( )
nn
Processable Polyelectrolyte
Δ
P. M. Lahti, D. A. Modarelli, F. R. Denton, III, R. W. Lenz, F. E. Karasz J. Am. Chem. Soc.
L. Hontis, V. Vrindts, D. Vanderzande, L. Lutsen Macromolecules, Vol. 36, No. 9, 20031988, 110, 7258
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The Last Challenge:e ast C a e geLinear Polyacenesy
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The Lower Oligoacenes
Polyacenes??o yace es??
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AcenesAcenes
Surprisingly, we have discovered that at the
tripletRB3LYP/6-31G(d) level of theory, the wavefunction for as small an oligoacene ashexacene (and all longer oligoacenes) becomes
close shell
hexacene (and all longer oligoacenes) becomesunstable.Re-optimization using the unrestricted
open shellRe-optimization, using the unrestrictedbroken symmetry B3LYP method (UB3LYP),leads to a singlet state with large amounts ofg gdiradical character.
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HOMO LUMO G i AHOMO-LUMO Gap in Acenes
8.0
eV)
Cl d h ll
4.0
6.0
MO
gap
(e Closed shellBiradical
0 0
2.0
OM
O-L
UM
0.00 2 4 6 8 10
Acene
H
Plateau at ca. 1.8 eV
Bendikov, M.; Duong, H.M.; Starkey, K.; Houk, K.N.; Carter, E.A.; Wudl, F.; J. Am. Chem. Soc., 2004, 126(24) 7416
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A t i l b dAcenes, terminal bond
1.4351.440
1 4101.4151.4201.4251.430
Close shellBiradicalT i l t
1.3901.3951.4001.4051.410 Triplet
0 2 4 6 8 10
Acene
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Connection Between Band Theory and Molecular Orbital Theory
According to the Su-Schrieffer-Heeger (SSH) model, the cco d g o e Su Sc e e eege (SS ) ode , eeffective length of a soliton in a σ-system is about 14 carbon atoms.
This is in agreement with our calculations, predicting diradical character in oligoacenes, and thus, hexacene-gheptacene have already enough σ -length (two 13-15 carbon atom chains, respectively) to produce two oligoacetylene
litsolitons.
The instabilities found for heptacene-octacene appear toThe instabilities found for heptacene-octacene appear to indicate that they are the “connector” between band theory and molecular orbital theory.y
Heeger, A. J.; Kivelson, S.; Schrieffer, J. R.; Su, W.-P. Rev. Mod. Phys. 1988, 60, 781.
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Spin Densityp y
Bendikov, M.; Duong, H.M.; Starkey, K.; Houk, K.N.; Carter, E.A.; Wudl, F.; J. Am. Chem. Soc., 2004, 126(24) 7416
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Summary
In contrast to the common view that acenes are closed shellsystems or have triplet ground states, we predict that largeroligoacenes possess an open-shell singlet ground state,where the triplet lies above singlet.
We have shown computationally that oligoacenes andprobably a variety of polyacene derivatives and analoguesp y y p y gshould exhibit a nonzero band gap.
It should be possible to prepare a linear polyacene, providedit is formed as a solid, with minimum lifetime in solution. Inanalogy with oligoenes vs polyacetyleneanalogy with oligoenes vs polyacetylene.
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EXPERIMENTAL RESULTS
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Matrix Isolated Heptacene
R. Mondal, B. K. Shah, D. C. Neckers J. Am. Chem. Soc. 2006, 128, 9612
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R. Mondal, B. K. Shah, D. C. Neckers J. Am. Chem. Soc. 2006, 128, 9612
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Isolable But Very Short-Lived Substituted Heptacene
Marcia M. Payne, Sean R. Parkin, and John E. Anthony 2005, 127, 8028
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Marcia M. Payne, Sean R. Parkin, and John E. Anthony 2005, 127, 8028
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Marcia M. Payne, Sean R. Parkin, and John E. Anthony 2005, 127, 8028
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TIPS ACETYLENE TETRAARYLHEPTACENE ISOLABLE AND RELATIVELY STABLE
Si(iPr) SiSi(iP )
Br
B
OBr
Br
Si(iPr)3 SiSi(iPr)3
PhPh
O Oa b c
Ph Ph
BrO
Br
Si(iPr)3 SiSi(iPr)3
PhPhPh Ph
a, (i) TipsCCLi (ii) SnCl2; b, LTMP/DPIBF; c, Zn/AcOH
D. Chun, F. Wudl, unpublished
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CRYSTAL STRUCTURE OF BIS(TIPSTHYNYL) TETRAPHENYL HEPTACENE
QuickTime™ and aTIFF (LZW) decompressor
are needed to see this picture.
D. Chun, F. Wudl, unpublished
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Electronic Spectroscopy
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PHOTOINDUCED OXYGEN DEGRADATION
Si SiSi
PhPh
Si
PhPh O
OO2
Si
PhPh
Si
PhPh
Ohν
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LIMITED CYCLIC VOLTAMMETRY
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Photoinduced Charge Generation
H. F. Bettinger, R. Mondalb and D. C. Neckers Chem. Commun., 2007, 5209