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Fluorescent molecular rotors based on the BODIPY motif: effect of remote substituents

Lookup NU author(s): Effat Bahaidarah, Emeritus Professor Anthony Harriman, Patrycja Stachelek, Dr Sandra Rihn

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Abstract

The ability of an unconstrained boron dipyrromethene dye to report on changes in local viscosity is improved by appending a single aryl ring at the lower rim of the dipyrrin core. Recovering the symmetry by attaching an identical aryl ring on the opposite side of the lower rim greatly diminishes the sensory activity, as does blocking rotation of the meso-aryl group. On the basis of viscosity- and temperature-dependence studies, together with quantum chemical calculations, it is proposed that a single aryl ring at the 3-position extends the molecular surface area that undergoes structural distortion during internal rotation. The substitution pattern at the lower rim also affects the harmonic frequencies at the bottom of the potential well and at the top of the barrier. These effects can be correlated with the separation of the H-1, H-7 hydrogen atoms.


Publication metadata

Author(s): Bahaidarah E, Harriman A, Stachelek P, Rihn S, Heyer E, Ziessel R

Publication type: Article

Publication status: Published

Journal: Photochemical & Photobiological Sciences

Year: 2014

Volume: 13

Issue: 10

Pages: 1397-1401

Online publication date: 28/07/2014

Acceptance date: 28/07/2014

ISSN (print): 1474-905X

ISSN (electronic): 1474-9092

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/C4PP00204K

DOI: 10.1039/c4pp00204k


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