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Substituent correlations characterized by Hammett constants in the Spiropyran-Merocyanine transition

: Brügner, O.; Reichenbach, T.; Sommer, M.; Walter, M.

Postprint urn:nbn:de:0011-n-4705012 (713 KByte PDF)
MD5 Fingerprint: e12f7acfc7a50a22d886ed7585c48e5a
Created on: 16.03.2018

Journal of physical chemistry. A 121 (2017), No.13, pp.2683-2687
ISSN: 1089-5639
Deutsche Forschungsgemeinschaft DFG
WA 1687/9
Journal Article, Electronic Publication
Fraunhofer IWM ()

The modification of molecular properties by the use of substituents is a versatile route for molecular design. Here we show for the example of multiresponsive spiropyrans that substituent effects and their correlations can be accurately described by Hammett constants, which in turn can be obtained directly from density functional theory calculations. The internal energetic difference ΔU between the noncolored and the colored form is determined for 63 spiropyran derivatives with substituents at the spiropyran N- and C6-positions, and can be described by only five parameters with an accuracy better than 0.1 eV (9.75 kJ/mol) using Hammett constants. This enables the prediction of ΔU values for other substituents without the need for further calculations nor experiments.