Subphthalocyanines:  Singular Nonplanar Aromatic CompoundsSynthesis, Reactivity, and Physical Properties

Fabrication and Characterization of Molecular Films of 11-Oxa[9]helicene and 9-Diethyleneglycoxy-11-oxa[9]helicene

“…The absorption peaks appeared at 300-350 nm ascribed to a π-π* transition, which is archetypal to fused aromatic compounds [11,12,18]. The peaks at 380-430 nm would be attributed to the n-π* transition from oxygen atoms connecting to helicene rings [18,19] and/or oxygen atom of ethylene glycol group [20]. Similar absorption behavior was found in the films except the corresponding bands were red-shifted to about 3-5 nm.…”

Synthesis and structure of the coordinatively unsaturated boron subphthalocyanine cation, [B(SubPc)]+

“…Too small to fit as a single atom into traditional tetraazamacrocycles such as porphyrins or phthalocyanines, boron forms a stable complex with the triazamacrocycle, subphthalocyanine [5]. Indeed, the subphthalocyanine macrocycle is stable only when coordinated to boron, typically as the four-coordinate B(SubPc)Cl complex, 1.…”

Synthetic approaches to asymmetric phthalocyanines and their analogues

“…183 These bowl-shaped aromatic macrocycles have effective C 3v symmetry and could be easily prepared by the reaction between substituted or unsubstituted phthalonitrile and BX 3 (X = F, Cl, Br). In 1988 and then in 1990, Ando and Mori 99,184 as well as Kobayashi and co-workers in 1990 100 found that SubPcs undergo ring expansion reaction when treated with 1,3-diaminoisoindoline or its analogues, resulting in the metal-free asymmetric A 3 B phthalocyanines (Schemes 14-15).…”