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J Am Chem Soc. 2010 Jan 20;132(2):580-6. doi: 10.1021/ja906917r.

Electronic properties of pentacene versus triisopropylsilylethynyl-substituted pentacene: environment-dependent effects of the silyl substituent.

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Department of Chemistry and Biochemistry, The University of Arizona, Tucson, Arizona 85721, USA.


Energy measures of the intra- and intermolecular electronic effects of triisopropylsilylethynyl substitution on pentacene have been obtained from the combination of closely related gas phase and solid phase ultraviolet photoelectron spectroscopy (UPS) measurements along with solution electrochemical measurements. The results show that the shift to lower ionization energy that is expected with this substitution and observed in the gas phase measurements becomes negligible in solution and is even reversed in the solid phase. The principles that emerge from this analysis are supported by electronic structure calculations at the density functional theory level. The relation between the gas phase and solid phase UPS measurements illustrated here provides a general approach to investigating the electronic effects acting on molecules in the condensed phase, which in this case are greater than the direct substituent electronic effects within the molecule. Electronic properties such as lower ionization energies built into the single-molecule building blocks of materials and devices may be reversed in the solid state.

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