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Ortho ‐ vs Bay ‐Functionalization: A Comparative Study on Tetracyano‐Terrylenediimides
Author(s) -
Battagliarin Glauco,
Puniredd Sreenivasa Reddy,
Stappert Sebastian,
Zajaczkowski Wojciech,
Wang Suhao,
Li Chen,
Pisula Wojciech,
Müllen Klaus
Publication year - 2014
Publication title -
advanced functional materials
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 6.069
H-Index - 322
eISSN - 1616-3028
pISSN - 1616-301X
DOI - 10.1002/adfm.201401573
Subject(s) - materials science , surface modification , planarity testing , semiconductor , solvent , dissolution , intermolecular force , electron mobility , drop (telecommunication) , nanotechnology , field effect transistor , charge carrier , diffusion , molecule , chemical engineering , transistor , chemical physics , crystallography , organic chemistry , optoelectronics , chemistry , thermodynamics , telecommunications , physics , quantum mechanics , voltage , computer science , engineering
In this paper n‐type semiconductors synthesized via selective fourfold cyanation of the ortho ‐ and bay ‐positions (2,5,10,13‐ and 1,6,9,14‐positions respectively) of teyrrylenediimides are reported. A detailed study about the impact of the diverse functionalization topologies on the optoelectronic properties, self‐organization from solution, solid‐state packing, and charge carrier transport in field‐effect transistors is presented. The ortho ‐substitution preserves the planarity of the core and favors high order in solution processed films. However, the strong intermolecular interactions lead to a microstructure with large aggregates and pronounced grain boundaries which lower the charge carrier transport in transistors. In contrast, the well‐soluble bay ‐functionalized terrylenediimide forms only disordered films which surprisingly result in n‐type average mobilities of 0.17 cm 2 /Vs after drop‐casting with similar values in air. Processing by solvent vapor diffusion enhances the transport to 0.65 cm 2 /Vs by slight improvement of the order and surface arrangement of the molecules. This mobility is comparable to highest n‐type conductivities measured for solution processed PDI derivatives demonstrating the high potential of TDI‐based semiconductors.