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Rigidified Push–Pull Dyes: Using Chromophore Size, Donor, and Acceptor Units to Tune the Ground State between Neutral and the Cyanine Limit

Rigidified Push–Pull Dyes: Using Chromophore Size, Donor, and Acceptor Units to Tune the Ground... A series of rigidified dyes with either dodecyloxy or piperidyl donors in combination with either malononitrile or barbiturate acceptors were synthesized. To analyze the influence of varying the donor (piperidyl vs. dodecyloxy), chromophore (mono‐, bis‐, or tricyclic system), and acceptor moiety (methyl barbiturate vs. malononitrile) on the ground‐state polarity, a combination of several methods was employed: UV/Vis absorption and emission, quantum chemical computations, 1H as well as 13C NMR spectroscopy, and cyclic voltammetry measurements. Depending on the acceptor and donor moieties, the ground state was shifted from a neutral form to the cyanine limit and further to a zwitterionic structure. When the dye had strong piperidyl donor and barbiturate acceptor substituents, the ground state was close to the cyanine limit, which resulted in strong cyanine‐like absorption properties with a dominant 0–0 transition. When the dye combined a weak dodecyloxy donor with a malononitrile or barbiturate acceptor, the neutral resonance form significantly contributed to the ground state, leading to weaker but broader absorption spectra featuring transitions to higher vibronic states. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png ChemPlusChem Wiley

Rigidified Push–Pull Dyes: Using Chromophore Size, Donor, and Acceptor Units to Tune the Ground State between Neutral and the Cyanine Limit

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References (100)

Publisher
Wiley
Copyright
© 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2192-6506
eISSN
2192-6506
DOI
10.1002/cplu.201700347
Publisher site
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Abstract

A series of rigidified dyes with either dodecyloxy or piperidyl donors in combination with either malononitrile or barbiturate acceptors were synthesized. To analyze the influence of varying the donor (piperidyl vs. dodecyloxy), chromophore (mono‐, bis‐, or tricyclic system), and acceptor moiety (methyl barbiturate vs. malononitrile) on the ground‐state polarity, a combination of several methods was employed: UV/Vis absorption and emission, quantum chemical computations, 1H as well as 13C NMR spectroscopy, and cyclic voltammetry measurements. Depending on the acceptor and donor moieties, the ground state was shifted from a neutral form to the cyanine limit and further to a zwitterionic structure. When the dye had strong piperidyl donor and barbiturate acceptor substituents, the ground state was close to the cyanine limit, which resulted in strong cyanine‐like absorption properties with a dominant 0–0 transition. When the dye combined a weak dodecyloxy donor with a malononitrile or barbiturate acceptor, the neutral resonance form significantly contributed to the ground state, leading to weaker but broader absorption spectra featuring transitions to higher vibronic states.

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ChemPlusChem – Wiley

Published: Sep 1, 2017

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