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Optoelectronic Properties of Chloro- and Fluoro- Boron Subphthalocyanine Derivatives: Theoretical, Synthetic and Spectral Studies

[ Vol. 7 , Issue. 3 ]

Author(s):

Alexander Schultheiss and Darlene K. Taylor*   Pages 210 - 217 ( 8 )

Abstract:


Aims: Experimental and computational studies of a series of multi-halogenated boron subphthalocyanine (Cl-BsubPcXn) derivatives are reported. This family of compounds with various degrees of chlorine or fluorine peripheral substitution (n = 4, 8, or 12) was studied by density functional theory (B3LYP model) in order to characterize the optimized geometries and electronic structures.

Method: The boron subphthalocyanines with one, two and three fully fluorinated rings (Cl- BsubPcF4, Cl-BsubPc F8, and Cl-BsubPcF12 respectively) were prepared in a single pot synthesis, purified, and characterized.

Observation: While the yields (0.6%, 5.2%, 1.9% respectively) are low, this is the first report of isolated separation and characterization of these subphthalocyanine structures.

Result: Absorption spectroscopy and electrochemical studies confirmed that the ring substitution has a strong effect on the electronic properties of Cl-BsubPcXn. Cyclic voltammetry and UV-Vis support theoretical results where bandgaps decreased as the degree of fluorine substitution increased.

Keywords:

Subphthalocyanines, halogen, optical property, HOMO, LUMO, peripheral substitution.

Affiliation:

Department of Chemistry, North Carolina Central University, Durham, NC, 27707, Department of Chemistry, North Carolina Central University, Durham, NC, 27707

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