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- Title
Comparative analysis of the energy levels of planar and core-twisted perylene bisimides in solution and solid state by UV/VIS, CV, and UPS/IPES.
- Authors
Arantes, C.; Scholz, M.; Schmidt, R.; Dehm, V.; Rocco, M.; Schöll, A.; Reinert, F.; Würthner, F.
- Abstract
The frontier orbital energies of four different functionalized perylene bisimide derivatives, PBI-Ph(iPr), PBI-H, PBI-F and PBI-Cl, were directly determined by UV-photo electron spectroscopy (UPS) and inverse photo electron spectroscopy (IPES) and are compared to the results from cyclic voltammetry (CV) and optical absorption spectroscopy (UV/VIS). The optical spectra reveal significant differences between monomeric species in solution and assembled molecules in the condensed state for the nearly planar PBI-H and PBI-F, which are attributed to significant π- π stacking interactions in the condensed phase. In contrast, for PBIs with bulky substituents or twisted core, i.e. 2,6-isopropylphenyl substituents at the imide positions (PBI-Ph(iPr)) or four chlorine substituents at perylene bay positions (PBI-Cl), similar spectra are observed in solution and in the condensed state, which suggests the absence of strong intermolecular π- π stacking interactions. An entirely different result is obtained for the HOMO/LUMO energy values obtained from UPS/IPES and CV measurements which do not reveal a significant impact of intermolecular π- π stacking interactions. When comparing CV and UPS/IPES results, an accentuated deviation was observed for the perylene bisimide derivatives as compared to correlations found in the literature.
- Subjects
PERYLENE derivatives; BISIMIDES; COMPARATIVE studies; FORCE &; energy; SOLUTION (Chemistry); SOLID state chemistry; ULTRAVIOLET radiation
- Publication
Applied Physics A: Materials Science & Processing, 2012, Vol 108, Issue 3, p629
- ISSN
0947-8396
- Publication type
Article
- DOI
10.1007/s00339-012-6941-3