Two semiconducting naphthalene bisimides were comparatively studied: NBI�(TAA)2, symmetrically N-substituted with triaryl amine and asymmetric NBI�TAA�Oc with triaryl amine and octyl N-substituents. Both compounds show very similar spectroscopic and redox properties but differ in their supramolecular organization. As evidenced by STM, in monolayers deposited on HOPG they form ordered 2D structures, however of different packing patterns. NBI�(TAA)2 does not form ordered 3D structures, yielding amorphous thin films whereas films of NBI�TAA�Oc are highly crystalline. Cyclic voltammetry and DFT calculations predict that both semiconductors should exhibit ambipolar behavior. Indeed, NBI�TAA�Oc is ambipolar[1], showing comparable mobilities of electrons and holes. NBI�(TAA)2 is not ambipolar and yields field effect only in the p-channel configuration[2,3]. This different behavior is rationalized on the basis of structural factors. This work has been financially supported by the FP-7, NoE/ICT, FLEXNET Contract No 247745, 2010 � 2012 and the European Union in the framework of European Social Fund through the Warsaw University of Technology Development Programme, realized by Center for Advanced Studies.[1] R. Rybakiewicz, J. Zapala, D. Djurado, R. Nowakowski, P. Toman, J. Pfleger, J.-M. Verilhac, M. Zagorska, A. Pron, Phys. Chem. Chem. Phys., 2013 , 15, 1578-1587. [2] A. Pron, R. R. Reghu, R. Rybakiewicz, H. Cybulski, D. Djurado, J. V. Grazulevicius, M. Zagorska, I. Kulszewicz-Bajer, J.-M. Verilhac, J. Phys. Chem. C, 2011 , 115, 15008�15017. [3] R. Rybakiewicz, D. Djurado, H. Cybulski, E. Dobrzynska, I. Kulszewicz-Bajer, D.Boudinet, J. M. Verilhac, M. Zagorska, A. Pron,Synth. Met., 2011 , 161, 1600� 1610.

Spectroscopic, electrochemical, electronic, and self-assembly properties of naphthalene bisimides asymmetrically and symmetrically <i>N</i>-substituted with triarylamine

246th National Meeting (2013)

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Spectroscopic, electrochemical, electronic, and self-assembly properties of naphthalene bisimides asymmetrically and symmetrically N-substituted with triarylamine