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by Margherita Durso
October 2008: B. Sc. in Chemistry – University of Bologna (“G. Ciamician” department). March 2011: M. Sc. in Organic Synthesis – University of Bologna (“G. Ciamician” department).
October 2011/at present – ISOF-CNR. Research fellow PhD student in Chemical Science – University of Bologna (supervisor Prof. M. Bandini).
J. Am. Chem. Soc. 2013, 135, 6724−6746.
n-type p-type + -
GREENCHEMISTRY
µ p = 9.13 x 10-3 cm2/Vs µ n = 2.94 x 10-2 cm2/Vs VDS ≈ -200 V S. Hotta et al. Appl. Phys. Lett. 90, 162108 (2007).
µ p = 1.5 x 10-3 cm2/Vs µ n = 2.5 x 10-5 cm2/Vs VDS ≈ -100 V ƞPL= 20%, EQE ≈ 0.5 %
A. Toshimita et al. Appl. Phys. Lett. 90, 171118 (2007).
• Ambipolar OLET, Highly integrated devices • Low manufacturing costs (one layer) • Control of the emissive zone position
+
-
2,3-TBI molecular semiconductors
M. Melucci et al. Chem. Commun. 2011, 47, 11840.
ambipolar and electroluminescent
µh = 7 x 10-3 cm2/Vs (VT P = -27V) µe = 0.55 cm2/Vs (VT N = 10 V) QY film 1.3 % EQE 0,2 % EP 180 nW
Comparable to the state of the art achieved by a polymeric layer (F8BT, QY 80%). (H. Sirringhaus et al., Adv. Mater. 2012, 24, 2728.)
70 mm
S. Toffanin (ISMN-CNR)
M. Melucci et al. Patent PCT/IB2012/052503.
Molecular tailoring
M. Durso, et al. Chem. Commun. 2013, 49, 4298.
M. Durso, et al. submitted.
off
on
R. Capelli (ISMN-CNR).
M. Melucci et al. Chem. Mater. 2013, 25, 668-676.
EDG/Major p- type contribution EWG/Major n- type contribution
Desymmetrization
Comp. µ h
(cm2V-1s-1) VT
P/V Ion/Ioff µ e
(cm2V-1s-1) VT
N/V
OLET EP (nW)
HT4N 3.1x10-3 -17.5 104 2.8x10-5 10.9 8
FT4N 1,4x10-5 -39.5 104 0,011 19.1 50
NT4N 7x10-3 -26.7 105 0.55 10.0 180
EDG
EWG
EDG
EWG
Calculations F. De Angelis, M. G. LoBello (ISTM-CNR Pg)
XRD M. Gazzano (ISOF-CNR)
M. Monari (Unibo)
Desymmetrization
SS Calculations F. Gallino (SAES-GETTERS)
Other applications…
Two polymorphs with different fluorescence
D. Gentili, M. Durso et al., submitted.
Colour evolution with the temperature mesaured by FM (M. Cavallini)
Solution processing and patterning
Time-temperature integrator
I. Manet (ISOF)
(with A. Sagnella, V. Benfenati)
T. Posati, M. Durso et al., submitted.
Other applications…
(with A. Pistone, V. Benfenati)
50 µm 50 µm
Synthetic issues
Suzuki cross-coupling
Stille cross-coupling
Semiquantitative Y 85 % Y
From Cross-couplings to direct arylations
Cross-coupling reactions Direct arylations
Ackermann, L. et al. Angew. Chem. Int. Ed. 2009, 48, 9792-9826. Milstein, D., Stille, J. K. J. Am. Chem. Soc. 1979, 101, 4992-4998. Negishi, E., King, A. O., Okukado, N. J. Org. Chem. 1977, 42, 1821-1823. Miyaura, N., Yanagi, T., Suzuki, A. Synth. Commun. 1981, 11, 513-519.
Y = 75-88%
Three examples of bromination and metallation sensitive substrates
New classes of materials by direct arylation
Y = 67%
Y = 70% Y = 70%
M. Durso, et al. submitted.
Acknowledgments
Manuela Melucci Cristian Bettini Laura Favaretto
Massimo Zambianchi M. Gazzano
A. Zanelli I. Manet
V. Benfenati
R. Capelli S. Toffanin
M. Cavallini D. Gentili T. Posati
F. De Angelis M.G. Lobello
F. Gallino
Firb: ITALNANONET
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