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Cocrystal assembled by 1,4‐diiodotetrafluorobenzene and phenothiazine based on C—I…π/N/S halogen bond and other assisting interactions
Author(s) -
Wang Hui,
Jin Wei Jun
Publication year - 2017
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520617002918
Subject(s) - cocrystal , phenothiazine , halogen , chemistry , halogen bond , stereochemistry , medicinal chemistry , organic chemistry , molecule , hydrogen bond , pharmacology , biology , alkyl
The halogen‐bonded cocrystal of 1,4‐diiodotetrafluorobenzene (1,4‐DITFB) with the butterfly‐shape non‐planar heterocyclic compound phenothiazine (PHT) was successfully assembled by the conventional solution‐based method. X‐ray single‐crystal diffraction analysis reveals a 3:2 stoichiometric ratio for the cocrystal (1,4‐DITFB/PHT), and the cocrystal structure is constructed via C—I…π, C—I…N and C—I…S halogen bonds as well as other assisting interactions ( e.g. C—H…F/S hydrogen bond, C—H…H—C and C—F…F—C bonds). The small shift of the 1,4‐DITFB vibrational band to lower frequencies in FT–IR and Raman spectroscopies provide evidence to confirm the existence of the halogen bond. In addition, the non‐planarity of the PHT molecule in the cocrystal results in PHT emitting weak phosphorescence and relatively strong delayed fluorescence. Thus, a wide range of delayed fluorescence and weak phosphorescence could play a significant role in selecting a proper π‐conjugated system to engineer functional cocrystal and luminescent materials by halogen bonds.