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Issue 57, 2015
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Axially phenoxylated aluminum phthalocyanines and their application in organic photovoltaic cells

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Abstract

Novel axially phenoxylated aluminium phthalocyanines, pentafluorophenoxy aluminium phthalocyanine (F5PhO-AlPc) and p-nitrophenoxy aluminium phthalocyanine (NO2PhO-AlPc), were synthesized through a one-step reaction starting from the commonly used photoactive material, chloro aluminium phthalocyanine (Cl-AlPc), and the respective phenols. Reactions with other phenols did not yield corresponding AlPc derivatives. Optical, electrical, and thermal analyses were carried out on F5PhO-AlPc and NO2PhO-AlPc using UV-Vis measurements (solution and thin-film), cyclic voltammetry (CV), differential-pulse voltammetry (DPV), and thermogravimetric analysis (TGA). A simple thermodynamic model was used to explain the lack of reaction when Cl-AlPc was treated a variety of alkylated phenols. We noted a side reaction producing fluoro aluminium phthalocyanine (F-AlPc) when the synthesis of F5PhO-AlPc was attempted in DMF. The model also explains this observation. F5PhO-AlPc and NO2PhO-AlPc were integrated into organic photovoltaic devices (OPVs) both as electron-donating and as electron-accepting materials. The phenoxy-AlPcs enable an enhancement of the open-circuit voltage (VOC) of the OPVs when applied as either an electron donor or as an electron acceptor compared to Cl-AlPc. The results within the OPV, specifically the increased VOC, are consistent with the steric shielding effect seen in other OPVs.

Graphical abstract: Axially phenoxylated aluminum phthalocyanines and their application in organic photovoltaic cells

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Supplementary files

Article information


Submitted
19 Mar 2015
Accepted
07 May 2015
First published
07 May 2015

RSC Adv., 2015,5, 45731-45739
Article type
Paper
Author version available

Axially phenoxylated aluminum phthalocyanines and their application in organic photovoltaic cells

H. Raboui, M. AL-Amar, A. I. Abdelrahman and T. P. Bender, RSC Adv., 2015, 5, 45731
DOI: 10.1039/C5RA04919A

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