Ilgın Nar

o-Carborane, Ferrocene, and Phthalocyanine Triad for High-Mobility Organic Field-Effect Transistors

An unsymmetrical zinc phthalocyanine with ferrocenylcarborane linked to the phthalocyanine ring through a phenylethynyl spacer was designed for organic field-effect transistor (OFET). The unsymmetrical phthalocyanine derivatives were characterized using a wide range of spectroscopic and electrochemical methods. In particular, the ferrocenylcarborane structure was unambiguously revealed based on the single-crystal X-ray diffraction analysis. In-depth investigations of the electrochemical properties demonstrated that the ferrocenylcarborane insertion extended the electrochemical character of ferrocenylcarborane-substituted phthalocyanine (7). Moreover, in the anodic potential scans, the oxidative electropolymerization of etynylphthalocyanine (6) and 7 was recorded. To clarify the effect of the insertion of ferrocenylcarborane (2) on the field-effect mobility, solution-processed films of 2, 6, and 7 were used as an active layer to fabricate the bottom-gate top-contact OFET devices. An analysis of the output and transfer characteristics of the fabricated devices indicated that the phthalocyanine derivative functionalized with ferrocenylcarborane moiety has great potential in the production of high-mobility OFET.

Synthesis and photophysical properties of a porphyrin–BODIPY dyad and a porphyrin–o-carborane–BODIPY triad

A novel porphyrin–BODIPY dyad, where BODIPY acts as the central antenna, linked via the Sonogashira coupling reaction, and a novel porphyrin–o-carborane–BODIPY triad, where both porphyrin and BODIPY are covalently attached to the o-carborane, have been synthesised and characterised. X-ray crystallography confirmed a V-shaped triad molecule. Detailed studies on the photophysical properties revealed the excitation of the BODIPY dyad system, which selectively triggered an efficient resonance energy transfer to the porphyrin unit. The presence of the o-carborane group in the triad system significantly diminished the energy transfer efficiency from BODIPY to the porphyrin moiety, because of its quenching properties. Besides, the triad system displayed aggregation-enhanced emission in THF/water systems, due to the presence of the o-carborane unit. The in-depth investigation of the electrochemical properties demonstrated that o-carborane insertion extended the initial reduction potentials and shifted half waves from the anodic to the cathodic site.

Ferrocenyl Phthalocyanine as Donor in Non-Poly(3-hexylthiophen-2,5-diyl) Bulk Heterojunction Solar Cell

Bulk heterojunction (BHJ) solar cells might one day play a vital role in realizing low-cost and environmentally benign photovoltaic devices. In this work, a BHJ solar cell was designed, based on a hexadeca-substituted phthalocyanine (FcPc) with ferrocenyl linked to the phthalocyanine ring. Next, we sought to obtain more quantitative information about the usability of this newly synthesized compound as a donor material in BHJ solar cells. Thus, BHJs with the structure of indium tin oxide/poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate)/FcPc:[6,6]-phenyl-C61-butyric acid methyl ester (PCBM) blend/LiF/Al were fabricated and characterized. The effect of blend ratio (0.5-2.0) on the BHJ solar cell parameters was also investigated. Interesting results were obtained in FcPc and the PCBM blend-based BHJ solar cell under optimized conditions. Our results presented here demonstrate that BHJ devices employing FcPc as a donor has great potential for the development of highly efficient non-poly(3-hexylthiophen-2,5-diyl) photovoltaic devices.

Novel phthalocyanines containing azo chromophores; synthesis, characterization, photophysical, and electrochemical properties

A series of novel metal-free and zinc (II), copper (II), cobalt (II), and manganese (III) phthalocyanine complexes bearing peripheral 2,6-dimethyl-4-(4-tert-butyl-phenylazo)phenoxy units have been synthesized. Novel phthalonitrile derivative required for the preparation of these phthalocyanine complexes was prepared by a base-catalyzed nucleophilic aromatic nitro displacement of 4-nitrophthalonitrile with 2,6-dimethyl-4-(4-tert-butyl-phenylazo)phenol. The structures of these new compounds were characterized by using elemental analyses, proton and carbon nuclear magnetic resonance, Fourier transform infrared spectroscopy, ultraviolet–visible spectroscopy and mass spectrometry. The photophysical properties of metal-free and zinc(II) phthalocyanines were studied in tetrahydrofuran. The electrochemical properties of the phthalocyanine complexes were investigated by cyclic and square wave voltammetry.