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

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