Role of Structural Factors in the Nonlinear Optical Properties of Phthalocyanines and Related Compounds

Phthalocyanines: old dyes, new materials. Putting color in nanotechnology

Subphthalocyanines: singular nonplanar aromatic compounds-synthesis, reactivity, and physical properties.

A double-heterostructure boron subphthalocyanine chloride (SubPc)/C60 thin-film photovoltaic cell exhibits a more than doubled Voc compared to a conventional copper phthalocyanine (CuPc)/C60 cell under 1 sun AM1.5G simulated illumination. The lower oxidation potential of SubPc results in an increase in the energy difference between the lowest unoccupied molecular orbital of the acceptor-like material and the highest occupied molecular orbital of the donor-like material (referred to as the interface gap, Ig) by 400 meV. We attribute the significant increase in Voc to this increase in Ig.

Enhanced open-circuit voltage in subphthalocyanine/C60 organic photovoltaic cells.

The control of luminous radiation has extremely important implications for modern and future technologies as well as in medicine. In this Review, we detail chemical structures and their relevant photophysical features for various groups of materials, including organic dyes such as metalloporphyrins and metallophthalocyanines (and derivatives), other common organic materials, mixed metal complexes and clusters, fullerenes, dendrimeric nanocomposites, polymeric materials (organic and/or inorganic), inorganic semiconductors, and other nanoscopic materials, utilized or potentially useful for the realization of devices able to filter in a smart way an external radiation. The concept of smart is referred to the characteristic of those materials that are capable to filter the radiation in a dynamic way without the need of an ancillary system for the activation of the required transmission change. In particular, this Review gives emphasis to the nonlinear optical properties of photoactive materials for the functi...

Nonlinear Optical Materials for the Smart Filtering of Optical Radiation.

Novel boron(III) subphthalocyanines (SubPcs) soluble in organic solvents containing a variety of donor and acceptor substituent groups have been synthesized by boron trihalide-induced cyclotrimerization of adequately substituted derivatives of phthalonitrile in 1-chloronaphthalene. The choice of the substituents on the 1,2-dicyanobenzene derivatives has been made taking into account the high reactivity of the Lewis acid BCl3 toward many functional groups. Considering this limitation, we set out to synthesize phthalodinitriles equipped with iodo, nitro, alkyl- or arylthio, alkyl- or arylsulfonyl groups that are sufficiently stable under the required reaction conditions and also provide an easily accessible set of acceptor/donor substituents. The quadratic and cubic hyperpolarizabilities of these compounds as well as their linear optical and electrochemical properties have been measured by several techniques, including EFISH (at two wavelengths), HRS, and THG, steady-state and time-resolved absorption and f...

U. Keller

Papers

Synthesis and Nonlinear Optical, Photophysical, and Electrochemical Properties of Subphthalocyanines