Abstract
Porphyrinic compounds comprise a diverse group of materials which have in common the presence of one or more cyclic tetrapyrroles known as porphyrins in their molecular structures. The resulting aromaticity gives rise to the semiconducting properties that make these compounds of interest for a broad range of applications, including artificial photosynthesis, catalysis, molecular electronics, sensors, non-linear optics, and solar cells. In this brief review, the crystallographic attributes of porphyrins are emphasized. Examples are given showing how the structural orientations of the porphyrin macrocycle, and the inter-porphyrin covalent bonding present in multiporphyrins influence the semiconducting properties. Beginning with porphine, the simplest porphyrin, we discuss how the more complex structures that have been reported are described by adding peripheral substituents and internal metalation to the macrocycles. We illustrate how the conjugation of the π-bonding, and the presence of electron donor/acceptor pairs, which are the basis for the semiconducting properties, are affected by the crystallographic topology.
Highlights
Porphyrins are defined as a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their carbon atoms via methine (=CH–) bridges [1].Since the porphyrin macrocyclic structure was first proposed by Küster over a century ago [2], research in the field has grown dramatically, resulting in a vast body of literature, which is continuing to expand at a rapid pace
It is the objective of the present paper to provide a brief outline of what is known of porphyrin solid state structures from a crystallographic perspective, in the hope that it may be useful to materials scientists as they become involved with porphyrin research
Many of the promising materials applications for porphyrins will rely on optimization of solid
Summary
Porphyrins are defined as a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their carbon atoms via methine (=CH–) bridges [1]. Mean bond angles distances for porphine macrocycles are indicated in. These macrocycle dimensions are relatively constant for all porphyrins, including complex multiporphyrins, as well as the simpler porphine relativelyderivatives. Nomenclature of macrocycle atomic positions (a) numerical designation; and Figure 2. Å. The macrocycles themselves arethe planar, coplanar the other, individual undergo distortions upmore to a few tenths porphyrins, of Ångstroms,the termed with of each andmacrocycles stacked in amay rotated, offset manner.ofIn complex planarity or “doming”.
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