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Bio-Inspired Materials for Electronic Applications. Technion – Israel Institute of Technology. Prof. N. Tessler (Electrical Engineering) Prof . Y. Eichen (Chemistry). - PowerPoint PPT Presentation
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19/04/2005
Bio-Inspired Materials for Electronic Applications
Technion – Israel Institute of Technology
Prof. N. Tessler (Electrical Engineering)Prof. Y. Eichen (Chemistry)
19/04/2005
N. Tessler, O. Globerman, N. Rappaport, Y. Preezant, Y. Roichman, O. Solomesch, et al., "Conjugated Polymer Electronics – Engineering Materials and Devices," in Handbook of Conducting Polymers, T. A. Skotheim and J. R. Reynolds, Eds., ed London: CRC, 2006.
Y.-J. Yu, O. Solomeshch, H. Chechik, A. A. Goryunkov, R. F. Tuktarov, D. H. Choi, et al., "p-type doping in organic light emitting diodes based on fluorinated C60," Journal of Applied Physics, vol. 104, p. 124505, 2008.
O. Solomeshch, Y. J. Yu, V. Medvedev, A. Razin, B. Blumer-Ganon, Y. Eichen, et al., "Wide band gap cross-linkable semiconducting polymer LED," Synt. Met., vol. 157, pp. 841-845, 2007.
19/04/2005
J.C. ELLENBOGEN J.C. LOVE, PROC. OF THE IEEE, 2000, 88(3), 386
Many structures with exciting electrical properties may be drawn on paper
But
Most of them are just too difficult to make.
Organic Molecules as Semiconductors
19/04/2005
How is Complexity Achieved in Truly Complex Systems?
19/04/2005
How is Complexity Achieved in Truly Complex Systems?
AntibodiesThe molecular
machinery (peptides) used to
tackle Unknown problems
19/04/2005
NH3+
O
SH O
[Cys]
NH3+
OO
NH2
O
[Gln]
NH3+
OO
OO
[Glu]
NH3+
O
O
[Gly]
NH3+
ONH
+
NH
O
[His]
NH3+
O
O
[Ile]
NH3+
O
O
[Leu]
NH3+
ONH3+
O
[Lys]
NH3+
OS
O
[Met]
NH3+
O
O
[Phe]
NH2+
O
O
[Pro]
NH3+
OH
O
O
[Ser]
NH3+
OH O
O
[Thr]
NH3+
O
N
O
[Trp]
NH3+
O
OH
O
[Tyr]
NH3+
O
O
[Val]
NH3+
O
O
[Ala]
NH3+
O
O
OO
[Asp]
NH3+
O
O
NH2
O
[Asn]
NH3+
ON
NH2+
NH2
O
[Arg]
How is Complexity Achieved in Truly Complex Systems?
19/04/2005
O
O
OBase
PO
*O
*n
Phospho(di)ester world
Peptide world
Sequence Independent Syntheses - The Way Nature Deals with Complexity
NO
R
* *n
H
R1
19/04/2005
How is Complexity Achieved in Truly Complex Systems ?
NO
OH
R' H
H
H
NOH
O
R' H
H
H+
-H2O
N
O
R H
H
H
N
H
HR'
OH
O
Very Simply in the case of peptides
19/04/2005
Linker
XNH
R
OO
Solid Phase Peptide Synthesis
X= Amino protecting group
Deprotect a amino function
Repeat
Couple
XNH
R'OH
O
Linker
NH2R
OO
Linker
NHR
OO
OR'
NHX
NH
ROH
O
O
R'
NH2
19/04/2005
Peptide bond – p-conjugated
N ** n
O
H* N
+ *n
O
H
What is its role in extended conjugation?
N
O
HHRN+
O
HHRN
O
HR
H
N
R1 H
H On
R1 H
NH
*
O
*n =Amineleft handPeptide linker
+Biologically relevant core
+Carboxylic acidleft handPeptide linker
O
O
R1
R2n *
*
O
O
R1
n
left handlinker + Optoelectronic
Core + right handlinker
=
O
O
R1
R2
Electronic Peptide
Of the shelf peptide synthesizer
Electronic Peptides – The basic idea
The materials of organic displays
The materials of Nature
Electronic-grade Tailor-made
19/04/2005
Oligo- p-Conjugated Peptide-Like Systems
SO
NNH
OSN
H
OSN
HS
X
OR'
H
OSRHN
SRHNO
X R'
SO
X R'NH
OSRHN
SO
X R'NH
OSN
H
OSRHN
SO
NNH
OSN
H
OSRHN
HS
X
OR'
ON
HR
*
H
*n
“Insulating” sp3
“Conductive” sp2
N*
HS
O
*n
19/04/2005
SRHNO
O SupportSNH2 O
O Support
SO
O SupportNH
OSN
H
OSRHN
S OO HRHN
SO
O SupportNH
OSN
H
OSNH2
SO
O SupportNH
OSNH2S
O
O SupportNH
OSRHN
S OO HRHN
S OO HRHN
SS
O
O SupportNH
OSN
H
OSN
H
ORHN
Coupling
Coupling Deprotection
Deprotection
Coupling
Deprotection
Oligo- p-Conjugated Peptide-Like Systems
19/04/2005
Peptide Bonds – p-Conjugated or Not?O
N
H
O
N+
H
Can the Peptide Bond Serve As An Assembler for Electronic Materials ?
Or – will the material remain a semiconductor when such unit is used as a linker?
H2N H2N
dipeptide tripeptide
Absorption Emission
Electronic Continuity through the Peptide bond?
NH2-5I2-5T2-CO2Me
HOMO
LUMO
NO2-5T2-5T2-CO2Me
SO
O MeNH
OSO2N
SO
O MeNH
ONH 2N
CH3
N
Michelle Steel & Jerome Cornil, Mons Group
The conjugation through the peptide bond is possible
350 400 450 500 550 600Wavelength (nm)
Pho
tolu
min
esce
nce
O
O
NH2
NO
OO
OH
O
PL QE=25%
Can one successfully-introduce PPV analogs?
No quenching introduced by this bond despite its slight push-pull nature
N
NO O
N *OH
* 10
Of the shelf peptide synthesizer
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