A role for π–Br interactions in the solid-state molecular packing of para-halo-phenoxy-boronsubphthalocyanines (original) (raw)
Materials 4-Fluorophenol was purchased from TCI Company Ltd. (Portland, Oregon). 4-Chlorophenol, 4-bromophenol, and 4-iodophenol were obtained from Sigma Aldrich (Mississauga, Ontario, Canada). All reagents were used as received. Other common solvents, reagents and standard basic alumina (300 mesh) were purchased from Caledon Laboratories (Caledon, Ontario, Canada) and used as received. Cl-BsubPc was synthesized according to a previously described procedure. [1] Methods X-ray diffraction results were analyzed using PLATON 40M-version 250809 [2] for bond angles and lengths, and crystal packing images were generated using Mercury version 2.2. [3] All data sets were collected using a Nonius KappaCCD diffractometer equipped with an Oxford Cryostream variable temperature apparatus. Hydrogen positions were calculated. All nuclear magnetic resonance (NMR) spectra were acquired on a Varian Mercury 400 MHz system in deuterated chloroform with 0.05% (v/v) tetramethylsilane (TMS) as a 1 H NMR reference purchased from Cambridge Isotope Laboratories and used as received. All ultraviolet-visible (UV-Vis) spectroscopy was performed using PerkinElmer Lambda 25 in a PerkinElmer quartz cuvette with 10.00 mm path length. The progress of reactions was monitored using a Waters 2695 high pressure liquid chromatography (HPLC) separation module with a Waters 2998 photodiode array. A Waters 150 mm reverse phase Sunfire® C18 5μm column was used with HPLC grade acetonitrile (ACN, 1.2 mL/min isocratic) purchased from Caledon Laboratories as the eluent. Molecular level computer modeling was performed at the density functional theory level using the 6-31G* basis set with the B3LYP method in the SPARTAN '06 V102 software package, except for that of IPhO-BsubPc, which was performed using the 6-311G* basis set. Crystal level computer modeling was performed as follows: the crystallographic information files (.cif) were imported into Materials Studio version 5.0 (Accelrys Inc.) [4]. The aromatic pattern of the BsubPc ligand was recreated in the visualization window. Next, using the DMol 3 module [5,6] the electrostatic potential (ESP) surface was calculated at DFT level (fine quality) employing the PW91 functional and DNP basis set. The ESP surface was
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