Journal of Organic Chemistry, volume 82, issue 4, pages 1986-1995
Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization.
Publication type: Journal Article
Publication date: 2017-02-01
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Triphenylphosphine oxide forms halogen-bonded (XB) complexes with pentafluoroiodobenzene and a 1,4-diaryl-5-iodotriazole. The stability of these complexes is assessed computationally and by 31P NMR spectroscopy in toluene-d8 solution, where both complexes are weakly associated. This knowledge is applied to the design and synthesis of two self-complementary phosphine oxide-iodotriazole hybrids that incorporate a phosphine oxide XB acceptor and a 1,4-diphenyl-5-iodotriazole XB donor within the same molecule. The self-complementary design of these modules facilitates their assembly in both toluene-d8 and, surprisingly, DCM-d2 into dimers, with significant stabilities, through the formation of halogen-bonded diads. The stability of these assemblies is a result of significant levels of cooperative binding that is present in both solvents. The connection of two of these hybrid units together, using a flexible spacer, facilitates the aggregation of these modules in DCM-d2 solution, through halogen bonding, forming oligomeric assemblies.
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- We do not take into account publications without a DOI.
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Maugeri L. et al. Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization. // Journal of Organic Chemistry. 2017. Vol. 82. No. 4. pp. 1986-1995.
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Maugeri L., Lébl T., Cordes D. B., Slawin A. M. Z., Philp D. Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization. // Journal of Organic Chemistry. 2017. Vol. 82. No. 4. pp. 1986-1995.
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TY - JOUR
DO - 10.1021/acs.joc.6b02822
UR - https://doi.org/10.1021/acs.joc.6b02822
TI - Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization.
T2 - Journal of Organic Chemistry
AU - Cordes, David B.
AU - Philp, Douglas
AU - Maugeri, Leonardo
AU - Lébl, T.
AU - Slawin, Alexandra M. Z.
PY - 2017
DA - 2017/02/01 00:00:00
PB - American Chemical Society (ACS)
SP - 1986-1995
IS - 4
VL - 82
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2017_Maugeri,
author = {David B. Cordes and Douglas Philp and Leonardo Maugeri and T. Lébl and Alexandra M. Z. Slawin},
title = {Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization.},
journal = {Journal of Organic Chemistry},
year = {2017},
volume = {82},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.joc.6b02822},
number = {4},
pages = {1986--1995},
doi = {10.1021/acs.joc.6b02822}
}
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MLA
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Maugeri, Leonardo, et al. “Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization..” Journal of Organic Chemistry, vol. 82, no. 4, Feb. 2017, pp. 1986-1995. https://doi.org/10.1021/acs.joc.6b02822.