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Synthesis and Characterization of Mixed Fluorinated Phenylthio‐ Subphthalocyanines
Author(s) -
Sejdarasi Leart,
McAuliffe Katherine J.,
Corbin Brooke A.,
Trivedi Evan R.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701422
Subject(s) - bathochromic shift , chemistry , molecule , absorption (acoustics) , ring (chemistry) , infrared , stereochemistry , crystallography , materials science , organic chemistry , fluorescence , physics , optics , composite material
Subphthalocyanines (SPcs), a platform of tripyrrolic macrocycles, offer a combination of optical and physical properties that make them highly applicable in a variety of fields. Incorporation of low‐symmetry elements allows for fine tuning of these properties by synthetic design. Herein, we report the synthesis of mixed fluorinated phenylthio‐ SPcs of the forms SPc(A n B 3‐ n ) and SPc(A n C 3‐ n ) where ‘A’ is tetrafluorobenzo‐, ‘B’ is 1,4‐bis(phenylthio)benzo‐, and ‘C’ is 1,4‐bis(phenylthio)naphtho‐, and n is an integer 1–2. Appended thioethers have a deshielding effect on 19 F NMR spectra and prompt a bathochromic shift of electronic absorption and emission. Combined with increased aromaticity in the ‘AC’ series, phenylthio‐ groups shift SPc emission to the edge of the near infrared region (λ f =680 nm), highlighting the potential of these molecules for optical imaging.