Influence of heteroatom substitution in benzene rings on structural features and spectral properties of subphthalocyanine dyes

From chemical curiosity to versatile building blocks: unmasking the hidden potential of main-group phthalocyanines in organic field-effect transistors

“…For instance, the frontier MOs can be stabilized from the replacement of the benzo moiety for electron-deficient heterocycles, such as pyrazine, 63 thiophene, 64 and 1,2,5-chalcadiazoles. [65][66][67] On the other hand, when aromatic hydrocarbons [68][69][70] and heterocycles [71][72][73][74][75] are instead annulated to benzene, or even used to bridge other porphyrinoids, [76][77][78][79] the extension of p-conjugation leads to bathochromic shifts in the main absorption band (Q-band).…”

Perfluorinated Porphyrazines. 5. Perfluoro-a,b-dicyanostylbene: Molecular Structure and Derived (Sub)Porphyrazine Complexes with IIIa Group Elements

“…For B III complex of non-fluorinated hexaphenylsubporphyrazine and other aryl substituted subporphyrazines the very low fluorescence was also observed (Ф F < 0.001-0.03 [14] ). At the same time boron(III) complexes of more rigid 1,2,5-thiadiazole and pyrazine fused subporphyrazines exhibit stronger fluorescence (Ф F = 0.11-0.15 [23] ), and phenyl substitution on pyrazine rings even increases it (Ф F = 0.31 [22] ). Therefore we can make a general conclusion that aryl substituted porphyrazines and subporphyrazines are more sensitive to the factors causing deformation of the macrocycle and promoting radiationless deactivation of the excited states than more rigid (sub)porphyrazines with fused heteroarenes.…”

Novel axial substituted subphthalocyanine sensitized titanium dioxide H12SubPcB‐OPh2OH/TiO2 photocatalyst: Synthesis, density functional theory calculation, and photocatalytic properties

“…The entire quantum computations were executed with Gaussian 16 software package. [62] The crystal structure that was extracted from the single-crystal XRD was used as the initial geometry for density functional theory (DFT) calculation and optimized with hybrid density functional B3LYP [63] with 6-31G(d) basis sets at the DFT-D3 [64,65] level. The partial molecular orbital structures were made using the Gauss View software program, and the contribution of atomic orbitals to molecular orbitals was depicted via Multiwfn program.…”