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Phosphorus‐Based Heteropentacenes: Efficiently Tunable Materials for Organic n‐Type Semiconductors
Author(s) -
Dienes Yvonne,
Eggenstein Matthias,
Kárpáti Tamás,
Sutherland Todd C.,
Nyulászi László,
Baumgartner Thomas
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801549
Subject(s) - organic field effect transistor , ambipolar diffusion , materials science , semiconductor , photoluminescence , field effect transistor , organic semiconductor , reactivity (psychology) , electrochemistry , atom (system on chip) , phosphorus , transistor , nanotechnology , chemistry , optoelectronics , electrode , physics , medicine , plasma , alternative medicine , quantum mechanics , voltage , pathology , computer science , metallurgy , embedded system
Benzo‐condensed dithieno[3,2‐ b :2′,3′‐ d ]phospholes have been synthesized that allow convenient tuning of properties that are essential for application as semiconductor materials in organic field‐effect transistor (OFET) devices. The versatile reactivity of the trivalent phosphorus atom in these heteropentacenes provides access to a series of materials that show different photophysical properties, significantly different organization in the solid state, and distinctly different electrochemical properties that can be achieved by simple chemical modifications. The materials show strong photoluminescence in solution and in the solid state that depends on the electronic nature of the phosphorus center. Electrochemical studies revealed that the phosphorus atom intrinsically furnishes materials with n‐channel or ambipolar behavior, also depending on its electronic nature. The experimental data were verified by DFT quantum chemical calculations and suggest that the phosphorus‐based heteropentacenes could be excellent candidates for n‐channel OFET semiconductor materials.