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Pieterse K, Vekemans JA, Kooijman H, et al. Ladderlike oligomers; intramolecular hydrogen bonding, push-pull character, and electron affinity. Chemistry. 2000;6(24):4597-603doi: 10.1002/1521-3765(20001215)6:24<4597::aid-chem4597>3.0.co;2-4.
Pieterse, K., Vekemans, J. A., Kooijman, H., Spek, A. L., & Meijer, E. W. (2000). Ladderlike oligomers; intramolecular hydrogen bonding, push-pull character, and electron affinity. Chemistry (Weinheim an der Bergstrasse, Germany), 6(24), 4597-603. https://doi.org/10.1002/1521-3765(20001215)6:24<4597::aid-chem4597>3.0.co;2-4
Pieterse, K, et al. "Ladderlike oligomers; intramolecular hydrogen bonding, push-pull character, and electron affinity." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 6,24 (2000): 4597-603. doi: https://doi.org/10.1002/1521-3765(20001215)6:24<4597::aid-chem4597>3.0.co;2-4
Pieterse K, Vekemans JA, Kooijman H, Spek AL, Meijer EW. Ladderlike oligomers; intramolecular hydrogen bonding, push-pull character, and electron affinity. Chemistry. 2000 Dec 15;6(24):4597-603. doi: 10.1002/1521-3765(20001215)6:24<4597::aid-chem4597>3.0.co;2-4. PMID: 11192093.
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Chemistry. 2000 Dec 15;6(24):4597-603. doi: 10.1002/1521-3765(20001215)6:24<4597::aid-chem4597>3.0.co;2-4.

Ladderlike oligomers; intramolecular hydrogen bonding, push-pull character, and electron affinity.

Chemistry (Weinheim an der Bergstrasse, Germany)

K Pieterse, J A Vekemans, H Kooijman, A L Spek, E W Meijer

Affiliations

  1. Laboratory of Macromolecular and Organic Chemistry, Eindhoven University of Technology, The Netherlands.

PMID: 11192093 DOI: 10.1002/1521-3765(20001215)6:24<4597::aid-chem4597>3.0.co;2-4

Abstract

Symmetrical 2,5-bis(2-aminophenyl)pyrazines have been synthesized by application of the Stille coupling strategy. These cotrimers feature three important properties, namely strong intramolecular hydrogen bonding, push-pull character, and high electron affinity. The presence of intramolecular hydrogen bonds has been confirmed by 1H NMR, IR spectroscopy, and single-crystal X-ray diffraction. The hydrogen bond strength can be increased by substituting the amino groups with stronger electron-withdrawing functionalities. Despite the anticipated enhanced pi-conjugation through planarization, a hypsochromic shift was observed in the UV/Vis spectra, explained by a decrease in push-pull character. The electron affinity of the cotrimers was deduced from the first reduction potentials measured by cyclic voltammetry and is related to the electron-withdrawing character of the amino substituents. The results obtained have been compared with those of the corresponding 4-aminophenyl analogues and show that intramolecular hydrogen bonds can be used to design polymers with enhanced pi conjugation as well as a high electron affinity.

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