The synthesis and characterization of a new metal-free phthalocyanine substituted with four diloop macrocyclic moieties

Structures and spectroscopic properties of nonperipherally and peripherally substituted metal-free phthalocyanines: A substitution effect study based on density functional theory calculations

“…Novel metal-free phthalocyanines containing four 19-membered dithiadiazadioxa macrocycles show split Q bands at 707 and 689 nm and B bands at 334 and 281 nm [54], which correspond to the calculated electronic absorption bands of 6 at 612 and 600 nm and 329 and 292 nm, respectively. The calculated electronic absorption spectra of 6 can also find analogs in the recorded electronic absorption spectra of the symmetrically tetrasubstituted metal-free phthalocyanine with four 14-membered dioxadithia macrocycles, each of which is attached to a 15-membered crown ether, at 708 and 641 and 292 nm [55]. The calculated electronic absorption bands at 321, 362, 402, 471, 638, and 644 nm in the electronic absorption spectrum of 8 are similar to the observed bands at 296, 326, 368, 449, 656, and 707 nm for the metal-free phthalocyanine containing four 27-membered diazaheptathia macrocyclic moieties on the peripheral positions [56], respectively, and can also correspond with the absorption bands of the metal-free phthalocyanine containing four 18-membered tetrathiadiaza macrocycles moieties on the peripheral positions [57] and the metal-free phthalocyanine bearing eight 16-membered tetrathiamonoaza macrocycles in the peripheral positions [58].…”

Novel porphyrazines containing peripherally functionalized macrocyclic (N2O2, N2S2) units: Synthesis and characterization

“…A common feature of the 1 H NMR spectrum of 9 is the broad absorption caused probably by the aggregation of H 2 Pz 0 , which is frequently encountered at the concentration used for NMR measurements [25,35]. The inner core protons of this compound could also not be observed because of strong aggregation of the molecule [25,36,37]. 1 H NMR and 13 C NMR spectra of 8 and 9 were very similar to those of the precursor compounds 6 and 7.…”

Synthesis and characterization of new metal-free and nickel(II) phthalocyanines containing tetraazatrioxa macrotricyclic moieties

“…The inner core NeH protons of the metalfree phthalocyanine were also identified in the 1 H NMR spectrum. Strong shielding of the cavity protons in the phthalocyanine core of this compound was manifested by a broad resonance at d ¼ À4.11 ppm [28] at high concentration which could be attributed to the NH resonance and identified easily with deuterium exchange. In the 1 H NMR spectrum of compound (5), the signals related to aromatic and aliphatic protons of the macrotricycles and phthalocyanine skeleton gave the significant characteristic of the proposed structure.…”