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Halogen Bonding of Organoiodines and Triiodide Anions in (NMe 3 Ph) + Salts
Author(s) -
Peloquin Andrew J.,
Kobra Khadijatul,
Li Yuxuan,
McMillen Colin D.,
Pennington William T.
Publication year - 2021
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202100096
Subject(s) - triiodide , halogen bond , halogen , chemistry , iodide , crystallography , crystal structure , lattice energy , acceptor , salt (chemistry) , ion , inorganic chemistry , stereochemistry , organic chemistry , alkyl , physics , electrode , dye sensitized solar cell , electrolyte , condensed matter physics
To study the role of the triiodide (I 3 ) − anion in establishing various halogen bonding patterns, the trimethylphenylammonium iodide (NMe 3 PhI) salt was reacted with diiodine (I 2 ) in the presence of a series of organoiodines, tetraiodoethylene (TIE), 1,2‐diiodo‐3,4,5,6‐tetrafluorobenzene ( o ‐F 4 DIB), 1,4‐diiodo‐2,3,5,6‐tetrafluorobenzene ( p ‐F 4 DIB), and 1,3,5‐trifluoro‐2,4,6‐triiodobenzene (1,3,5‐F 3 I 3 B) to form cocrystals of the organoiodines with the trimethylphenylammonium triiodide (NMe 3 PhI 3 ) salt. Single‐crystal X‐ray crystallography revealed the (I 3 ) − anion served as a halogen bond acceptor for the organoiodine donors, forming a variety of 1‐D, 2‐D, and 3‐D packing arrangements through I⋅⋅⋅I halogen bonding. Significant asymmetry was observed within the (I 3 ) − anion. The melting points of the cocrystalline materials, as determined by simultaneous DSC/TGA, ranged from 43 °C to 119 °C and showed a strong dependence on the identity of the organoiodine incorporated into the crystal lattice.