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Al Ouahabi A, Baxter PN, Gisselbrecht JP, et al. Synthesis and properties of oligo[n]cruciforms: nanosized sterically encumbered tetraethynylphenyl-homologated fluorophores. J Org Chem. 2009;74(13):4675-89doi: 10.1021/jo802797e.
Al Ouahabi, A., Baxter, P. N., Gisselbrecht, J. P., De Cian, A., Brelot, L., & Kyritsakas-Gruber, N. (2009). Synthesis and properties of oligo[n]cruciforms: nanosized sterically encumbered tetraethynylphenyl-homologated fluorophores. The Journal of organic chemistry, 74(13), 4675-89. https://doi.org/10.1021/jo802797e
Al Ouahabi, Abdelaziz, et al. "Synthesis and properties of oligo[n]cruciforms: nanosized sterically encumbered tetraethynylphenyl-homologated fluorophores." The Journal of organic chemistry vol. 74,13 (2009): 4675-89. doi: https://doi.org/10.1021/jo802797e
Al Ouahabi A, Baxter PN, Gisselbrecht JP, De Cian A, Brelot L, Kyritsakas-Gruber N. Synthesis and properties of oligo[n]cruciforms: nanosized sterically encumbered tetraethynylphenyl-homologated fluorophores. J Org Chem. 2009 Jul 03;74(13):4675-89. doi: 10.1021/jo802797e. PMID: 19522488.
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J Org Chem. 2009 Jul 03;74(13):4675-89. doi: 10.1021/jo802797e.

Synthesis and properties of oligo[n]cruciforms: nanosized sterically encumbered tetraethynylphenyl-homologated fluorophores.

The Journal of organic chemistry

Abdelaziz Al Ouahabi, Paul N W Baxter, Jean-Paul Gisselbrecht, André De Cian, Lydia Brelot, Nathalie Kyritsakas-Gruber

Affiliations

  1. Institut Charles Sadron, CNRS UPR 022, 6 rue du Loess, F-67083 Strasbourg, France.

PMID: 19522488 DOI: 10.1021/jo802797e

Abstract

A series of nanosized phenyleneethynylenes have been prepared which are sterically insulated from the surrounding environment by multiple functionalization with triisopropylsilyl (TIPS) substituents. The phenyleneethynylenes comprise oligo[n]cruciforms 1-4 (n = 3-5) and a dehydrotribenzo[12]annulene 5, the former of which possess para-acyclic and the latter ortho-cyclic electronic conjugation pathways. All compounds were characterized by (1)H and (13)C NMR, IR, and mass spectroscopic techniques. The X-ray crystal structure of 1 confirmed the sterically isolating properties of the TIPS substituents. A comparison of the physical properties of these electronically differing systems revealed that they were all luminescent upon UV irradiation displayed negligible aggregation in dilute solution and that particular members of the series studied were electrochemically active, undergoing facile reversible reductions. The phenyleneethynylenes also exhibited significantly enhanced thermal stability by virtue of the presence of the TIPS substituents. The properties of 1-5 suggest that they are promising building blocks for the construction of materials for novel molecular electronics applications.

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