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Synthesis and Investigation of Nanomaterials for
      Potential Optoelectronic Applications




Dr. Bassam Alameddine
Research Interests: Functional Nanomaterials

                               Flat panel
                             displays (FED,
                              OLED, LCD)




          Photovoltaics
                          Optoelectronic        Organic
                            materials         Transistors




                               Sensors
Research Interests: Functional Nanomaterials

                               Build on-
                               demand
                              functional
                              molecules



                                                    Control
            Improve
                                                   down to
          adhesion at
                                                   molecular
           interfaces
                                                     level
                               Nano-
                              materials




                  Study the                Understand
                    self-                       the
                  assembly                  structure /
                     and                    properties
                   packing                 relationship
Synthesis of Non-Covalent Polymers
Synthesis of Perfluoroalkylated HBC
                                                                         R=                                     Abbreviation
                    R
                                                                                        perfluoroalkylated chains

     R                            R                                      -(CH2)2(CF2)6F                         Rf2,6
                                                                         -(CH2)2(CF2)8F                         Rf2,8
                                                                         -p-Ph(CH2)2(CF2)8F                     Ph-Rf2,8
                                                                         -(CH2)3(CF2)6F                         Rf3,6
                                                                         -(CH2)3(CF2)8F                         Rf3,8
                                                                         -(CH2)4(CF2)4F                         Rf4,4
     R                            R                                      -(CH2)4(CF2)6F                         Rf4,6
                                                                         -(CH2)4(CF2)8F                         Rf4,8
                    R                                                    -(CH2)4(CF2)10F                        Rf4,10
                                                                         -(CH2)5(CF2)6F                         Rf5,6
                                                                         -(CH2)5(CF2)8F                         Rf5,8
   Multistep syntheses (7-12 steps)                                     -(CH2)6(CF2)6F                         Rf6,6
                                                                         -(CH2)6(CF2)8F                         Rf6,8
                                                                         -(CH2)8(CF2)4F                         Rf8,4
   Insertion of CH2’s discard the EW                                    -(CH2)8(CF2)6F                         Rf8,6
                                                                         -(CH2)8(CF2)8F                         Rf8,8
       effect of the perfluoro chains and
                                                                                  perfluoroalkoxyphenyl substituents
       improve both solubility and yield
                                                                         -p-PhO(CH2)4(CF2)8F                    PhORf4,8
                                                                         -p-PhO(CH2)6(CF2)6F                    PhORf6,6
   Relatively good overall yields (13-                                           branched perfluoralkylated chains
       43%)                                                              -(CH2)3CH[CH2(CF2)4F]2                 Rf3,3,4,4
                                                                         -(CH2)3CH[CH2(CF2)6F]2                 Rf3,3,6,6

B. Alameddine, O. Aebischer, T. A. Jenny, Chimia 2008, 62, 967.
O. F. Aebischer, P. Tondo, B. Alameddine, T. A. Jenny, synthesis 2006, 17, 2891
Properties of Perfluoroalkylated HBCs
 All the perfluorinated HBCs are liquid crystalline over a wide temperature range (~280˚C)

 Introducing a phenyl group and increasing CF2 part leads to the formation of a lamellar phase
  (HBC-PhRf2,8 & HBC-PhORf4,8)

 Lateral aggregation highly affected by the solvent, conc., T and the perfluoroalkylated chain length

                              Cryo-SEM: A new tool to detect nanofilaments




      A 10-4 M in BTF affords free standing nanofilaments with a uniform size l ~ 750 nm and d ~ 30 nm

B. Alameddine, et al., Chem. Mater. 2005, 17, 4798
O. Aebischer, A. Aebischer, B. Alameddine, M. Dadras, H.-U. Güdel, T. Jenny, Chem. Commun. 2006, 4221
O. Aebischer, A. Aebischer, B. Donnio, B. Alameddine, M. Dadras, H.-U. Güdel, D. Guillon, T. A. Jenny, J. Mat. Chem. 2007, 17, 1262
Synthesis of Hole Transport Layers for OLEDs
Triarylamines for OLEDs: Properties
 Six step synthesis with good overall yields (50-60%)

 Both compounds emit in the blue (BNP at 430 nm and TND at 455 nm)

 Completely amorphous

     Rf8                  Rf8
                                                      Rf8
                 N
                                                                   Glassy solid produces
                                                                   fibers at RT
                                                  N

                 N
                                      Rf8                    Rf8
   Rf8
                                               BNP-Rf2,8
                          Rf8
                                                                                           X 100
             TND-Rf2,8



• Preliminary tests showed low efficiencies than standard HTL used in the market
• A shift in the redox potential by ~200 mV with the same molecules but with alkylated chains


          The CH2/CF2 ratio has to be tuned to decrease the EW effect of the fluorinated part

B. Alameddine, C. Savary, O. Aebischer, T. A. Jenny, synthesis 2007, 2, 271
Synthesis of Oligomers for Organic Transistors
Organic Materials for OTFTs
                                                             h    h h h        h h
                                                            h hh hh hh hh hh
                                                           h h h h        h h
                                                        hh h h h h h h h h h h                                 Amplification effect
                                                       h h h h         h h
                                     Source (Au) h  h h h h hh h h hh h h Drain (Au)                           upon increasing Vg
                                                  Organic Film (~40 nm)
                                       Thermally Passivated SiO2 (100 nm, 30 nF/cm2)
                                           Heavily n-doped Si (Gate, Res.= 2-4 Ω)

  In a two step synthesis:
                                                                                         C12H25   C12H25

                                                                        S                                           S

                                                                                   S                       S




                                                                                            Thermal evaporation on SiO2 treated with HMDS
                                                                                             μ ≈ 10-2 cm2.V-1.s-1
                            -6
                  -7.0x10              VG= 0V
                            -6         VG= -20V
                  -6.0x10              VG= -40V
                  -5.0x10
                            -6         VG= -60V

                  -4.0x10
                            -6
                                       VG= -80V
                                       VG= -100V                                             on/off ratio ≈ 2.6 x 104
         ID (A)




                            -6
                  -3.0x10
                  -2.0x10
                            -6
                                                                                            Ink-jet printed solution of the oligomer in TCB
                            -6
                  -1.0x10
                       0.0
                            -6
                                                                                             μ ≈ 5.4 x 10-4 cm2.V-1.s-1
                  1.0x10
                                 0      -20        -40            -60       -80   -100
                                                         VD (V)
                                                                                             on/off ≈ 6 x 103

S. Sanaur, A. Whalley, B. Alameddine, M. Carnes, C. Nuckolls, Organic Electronics 2006, 7, 423
Organic Materials for Monolayer Transistors
In a three step synthesis:
                                                    ~3.1 nm

                                                    C8H17   C8H17

                                 S                                         S

                                           S                        S

               HO                                                                        OH




                           30 – 100 nm spacing




   Source (Au)                         Drain (Au)
       3 nm Aluminum Oxide (ALD deposited)
       Heavily n-doped Si with 1 nm SiO2(Gate)




                                                                        μ ≈ 10-5 cm2.V-1.s-1

                                                                        on/off ≈ 103
Acquired Skills


 Advanced synthesis and characterization of organic and polymeric materials by
employing cutting-edge techniques

 Trained on working in a clean room

 Familiar with the different methods used for the deposition and characterization of
organic thin films

 Capability to design and assemble reactors for CVD processes and related techniques

 Set international collaborations necessary to excel in such a multidisciplinary field
Acknowledgment and Collaborations


  Dr. Walter Amrein                         Prof. Geoffrey Bodenhausen    Prof. Tomasz Wesolowski
  Oliver Scheidegger (MALDI-TOF analysis)   Dr. Jens Dittmer (SS-NMR)     Dr. Fabien Tran (Computational study)




 Dr. Noella Lemaitre                                                                  Prof. Louis Schlapbach
                                     Prof. Titus A. Jenny
 (OLED)                                                                               Dr. Oliver Groening
                                     Corinne Savary (Lab. technician)
                                                                                      Dr. Pascal Ruffieux
                                     Dr. Olivier Aebischer
                                                                                      (STM, FEDs)
                                     Patrick Tondo, Mauro Schindler
                                     (PhD students)




Dr. Massoud Dadras                          Prof. Robert Deschenaux        Prof. Daniel Guillon
Mireille LeBoeuf (SEM & TEM)                Dr. David Scanu (POM & DSC)    Dr. Bertrand Donnio (Powder XRD)
Acknowledgment and Collaborations




   Center for Electron Transport                                             Dr. Cherie Kagan
    in Molecular Nanostructures
                                                                             Dr. George Tulevski
  Prof. Horst Stormer
  Dr. Rachel Steiner
  Adam Whalley



                                                     Dr. Graciela Blanchet
                              Dr. Sébastien Sanaur   Dr. Xiang-Zheng Bo

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Research Interests Dr. Bassam Alameddine

  • 1. Synthesis and Investigation of Nanomaterials for Potential Optoelectronic Applications Dr. Bassam Alameddine
  • 2. Research Interests: Functional Nanomaterials Flat panel displays (FED, OLED, LCD) Photovoltaics Optoelectronic Organic materials Transistors Sensors
  • 3. Research Interests: Functional Nanomaterials Build on- demand functional molecules Control Improve down to adhesion at molecular interfaces level Nano- materials Study the Understand self- the assembly structure / and properties packing relationship
  • 5. Synthesis of Perfluoroalkylated HBC R= Abbreviation R perfluoroalkylated chains R R -(CH2)2(CF2)6F Rf2,6 -(CH2)2(CF2)8F Rf2,8 -p-Ph(CH2)2(CF2)8F Ph-Rf2,8 -(CH2)3(CF2)6F Rf3,6 -(CH2)3(CF2)8F Rf3,8 -(CH2)4(CF2)4F Rf4,4 R R -(CH2)4(CF2)6F Rf4,6 -(CH2)4(CF2)8F Rf4,8 R -(CH2)4(CF2)10F Rf4,10 -(CH2)5(CF2)6F Rf5,6 -(CH2)5(CF2)8F Rf5,8  Multistep syntheses (7-12 steps) -(CH2)6(CF2)6F Rf6,6 -(CH2)6(CF2)8F Rf6,8 -(CH2)8(CF2)4F Rf8,4  Insertion of CH2’s discard the EW -(CH2)8(CF2)6F Rf8,6 -(CH2)8(CF2)8F Rf8,8 effect of the perfluoro chains and perfluoroalkoxyphenyl substituents improve both solubility and yield -p-PhO(CH2)4(CF2)8F PhORf4,8 -p-PhO(CH2)6(CF2)6F PhORf6,6  Relatively good overall yields (13- branched perfluoralkylated chains 43%) -(CH2)3CH[CH2(CF2)4F]2 Rf3,3,4,4 -(CH2)3CH[CH2(CF2)6F]2 Rf3,3,6,6 B. Alameddine, O. Aebischer, T. A. Jenny, Chimia 2008, 62, 967. O. F. Aebischer, P. Tondo, B. Alameddine, T. A. Jenny, synthesis 2006, 17, 2891
  • 6. Properties of Perfluoroalkylated HBCs  All the perfluorinated HBCs are liquid crystalline over a wide temperature range (~280˚C)  Introducing a phenyl group and increasing CF2 part leads to the formation of a lamellar phase (HBC-PhRf2,8 & HBC-PhORf4,8)  Lateral aggregation highly affected by the solvent, conc., T and the perfluoroalkylated chain length  Cryo-SEM: A new tool to detect nanofilaments A 10-4 M in BTF affords free standing nanofilaments with a uniform size l ~ 750 nm and d ~ 30 nm B. Alameddine, et al., Chem. Mater. 2005, 17, 4798 O. Aebischer, A. Aebischer, B. Alameddine, M. Dadras, H.-U. Güdel, T. Jenny, Chem. Commun. 2006, 4221 O. Aebischer, A. Aebischer, B. Donnio, B. Alameddine, M. Dadras, H.-U. Güdel, D. Guillon, T. A. Jenny, J. Mat. Chem. 2007, 17, 1262
  • 7. Synthesis of Hole Transport Layers for OLEDs
  • 8. Triarylamines for OLEDs: Properties Six step synthesis with good overall yields (50-60%) Both compounds emit in the blue (BNP at 430 nm and TND at 455 nm) Completely amorphous Rf8 Rf8 Rf8 N Glassy solid produces fibers at RT N N Rf8 Rf8 Rf8 BNP-Rf2,8 Rf8 X 100 TND-Rf2,8 • Preliminary tests showed low efficiencies than standard HTL used in the market • A shift in the redox potential by ~200 mV with the same molecules but with alkylated chains  The CH2/CF2 ratio has to be tuned to decrease the EW effect of the fluorinated part B. Alameddine, C. Savary, O. Aebischer, T. A. Jenny, synthesis 2007, 2, 271
  • 9. Synthesis of Oligomers for Organic Transistors
  • 10. Organic Materials for OTFTs h h h h h h h hh hh hh hh hh h h h h h h hh h h h h h h h h h h Amplification effect h h h h h h Source (Au) h h h h h hh h h hh h h Drain (Au) upon increasing Vg Organic Film (~40 nm) Thermally Passivated SiO2 (100 nm, 30 nF/cm2) Heavily n-doped Si (Gate, Res.= 2-4 Ω) In a two step synthesis: C12H25 C12H25 S S S S Thermal evaporation on SiO2 treated with HMDS μ ≈ 10-2 cm2.V-1.s-1 -6 -7.0x10 VG= 0V -6 VG= -20V -6.0x10 VG= -40V -5.0x10 -6 VG= -60V -4.0x10 -6 VG= -80V VG= -100V on/off ratio ≈ 2.6 x 104 ID (A) -6 -3.0x10 -2.0x10 -6 Ink-jet printed solution of the oligomer in TCB -6 -1.0x10 0.0 -6 μ ≈ 5.4 x 10-4 cm2.V-1.s-1 1.0x10 0 -20 -40 -60 -80 -100 VD (V) on/off ≈ 6 x 103 S. Sanaur, A. Whalley, B. Alameddine, M. Carnes, C. Nuckolls, Organic Electronics 2006, 7, 423
  • 11. Organic Materials for Monolayer Transistors In a three step synthesis: ~3.1 nm C8H17 C8H17 S S S S HO OH 30 – 100 nm spacing Source (Au) Drain (Au) 3 nm Aluminum Oxide (ALD deposited) Heavily n-doped Si with 1 nm SiO2(Gate) μ ≈ 10-5 cm2.V-1.s-1 on/off ≈ 103
  • 12. Acquired Skills  Advanced synthesis and characterization of organic and polymeric materials by employing cutting-edge techniques  Trained on working in a clean room  Familiar with the different methods used for the deposition and characterization of organic thin films  Capability to design and assemble reactors for CVD processes and related techniques  Set international collaborations necessary to excel in such a multidisciplinary field
  • 13. Acknowledgment and Collaborations Dr. Walter Amrein Prof. Geoffrey Bodenhausen Prof. Tomasz Wesolowski Oliver Scheidegger (MALDI-TOF analysis) Dr. Jens Dittmer (SS-NMR) Dr. Fabien Tran (Computational study) Dr. Noella Lemaitre Prof. Louis Schlapbach Prof. Titus A. Jenny (OLED) Dr. Oliver Groening Corinne Savary (Lab. technician) Dr. Pascal Ruffieux Dr. Olivier Aebischer (STM, FEDs) Patrick Tondo, Mauro Schindler (PhD students) Dr. Massoud Dadras Prof. Robert Deschenaux Prof. Daniel Guillon Mireille LeBoeuf (SEM & TEM) Dr. David Scanu (POM & DSC) Dr. Bertrand Donnio (Powder XRD)
  • 14. Acknowledgment and Collaborations Center for Electron Transport Dr. Cherie Kagan in Molecular Nanostructures Dr. George Tulevski Prof. Horst Stormer Dr. Rachel Steiner Adam Whalley Dr. Graciela Blanchet Dr. Sébastien Sanaur Dr. Xiang-Zheng Bo