Towards chiral 1,2-naphthalocyanines: syntheses of the pure geometrical isomers of the magnesium and lutetium complexes

Abstract

<jats:p> Planar 1,2-naphthalocyanines present four different geometrical isomers of C<jats:sub>4h</jats:sub>, C<jats:sub>2v</jats:sub>, D<jats:sub>2h</jats:sub> and C<jats:sub>s</jats:sub> symmetries. In the case of magnesium complexes these four isomers have been isolated and characterized for the first time. The C<jats:sub>4h</jats:sub> and C<jats:sub>s</jats:sub> isomers of the magnesium complexes have been transformed in two steps into the corresponding lutetium mononaphthalocyanines 1,2-NcLuX. </jats:p>

Syntheses and Functional Properties of Phthalocyanines

“…Zinc non-peripheral phthalocyanine derivatives having long side chains formed an aggregation at least 10 −5 mol·L -1 in cyclohexane [9,78]. It is enough thought that the samples in this study for laser-flash photolysis were formed in aggregation in the experimental condition.…”

“…The assignment of the Q band from each fraction was carried out on the theory of the relationship between symmetry and the Q band [ 1 , 4 , 74 , 75 , 76 , 77 ]. The Q band splits into two peaks of the highest isomer symmetry, the splitting Q band is decreased with a decreasing symmetry [ 78 ]. The symmetry of the position isomer of 5c was decreased in orders of C 2h , D 2h , C 2v , C s [ 79 ].…”

“…Unfortunately, a precise explanation for this cannot be provided, but it seems to be due to the following phenomenon: phthalocyanine derivatives were well known to aggregate in water and non-coordinating solvents. Zinc non-peripheral phthalocyanine derivatives having long side chains formed an aggregation at least 10 −5 mol·L -1 in cyclohexane [ 9 , 78 ]. It is enough thought that the samples in this study for laser-flash photolysis were formed in aggregation in the experimental condition.…”

“…The photoexcited triplet state lifetime of 6 was estimated for 20 s laser pulse. The transient absorption was assigned to a triplet state [ 78 ].…”

Novel soluble thieno[3,2-b]thiophene fused porphyrazine

“…1 H NMR (400 MHz, CDCl 3 ) d 6.91 (t, J ¼ 1.0 Hz, 1H), 2.88-2.83 (m, 2H), 1.74-1.66 (m, 2H), 1.41-1.21 (m, 10H), 0.88 (t, J ¼ 7.1 Hz, 3H). 13 2,3-Dicyano-5-octylthieno[3,2-b]thiophene (7). CuCN (2.55 g, 28.5 mmol) and 5 (1.46 g, 3.56 mmol) were added to a 25 mL round bottomed ask.…”