Subphthalocyanine-type dye with enhanced electron affinity: Effect of combined azasubstitution and peripheral chlorination

Recent advances in subphthalocyanines and related subporphyrinoids

“…The latter is reflected in the cyclovoltammetric study of 290 , which shows its first reduction potential at E 1/2 = −1.248 V vs. Fc/Fc + , that is, 472 mV easier to reduce than SubPz 276 . 530 The introduction of six chlorine atoms at the pyrazine rings shift this value still more anodic at −0.168 V. 534…”

“…81). 64,530–535 All of these Subpyrazinoporphyrazines have been prepared by cyclotrimerization reaction of the corresponding dinitrile derivatives, in the presence of BCl 3 , under classical conditions. The yields range from 0.3% for 289 to 35% for 291 .…”

Analysis of the solvent effects on the crystal growth of peripherally chlorinated boron subphthalocyanines

“…For our study, we then began by looking through the Cambridge Crystallographic Data Centre (CCDC) and found that several solvents were incorporated into determined BsubPc single crystals: DCM, 36,[44][45][46][47][48][49] CHCl 3 , 50-58 H 2 O, 49,50,52,55,[59][60][61][62] acetone, 63 THF, 57,63 hexane, 64,65 and heptane. 66,67 Furthermore, aromatic solvents were also used for BsubPc crystal growth and found to be incorporated into their determined nano-structures, such as benzene, 23,35,36,52,56,[68][69][70][71] toluene, 53,56,[72][73][74][75] chlorobenzene, 15 and dichlorobenzene. 62,76 For a more in-depth example, a report outlines that the solvent is incorporated into the crystals when attempting to co-crystallize a BsubPc with a fullerene.…”

Electronic Structure, Bonding, and Stability of Boron Subphthalocyanine Halides and Pseudohalides

“…In parallel with this basic progress, BsubPcs have been shown to possess many desirable properties for multiple applications. They can be easily applied as dyes and pigments [ 26–30 ] but can also be applied as fluorescence sensors, [ 31–33 ] optical imaging materials, [ 34 ] and photodynamic therapy sensors. [ 35 ] Particularly for their optical properties, but also for their tunable chemical and thermal stabilities, low sublimation temperatures, and in some cases bipolar electrochemistry, BsubPcs have emerged as interesting semiconductors for organic photovoltaics (OPV) applications.…”

“…In parallel with this basic progress, BsubPcs have been shown to possess many desirable properties for multiple applications. They can be easily applied as dyes and pigments [26][27][28][29][30] but can also be applied as fluorescence sensors, [31][32][33] optical imaging materials, [34] and photodynamic therapy sensors. [35] Particularly for their optical properties, but also for their tunable chemical Stick and space filling model representation of Cl-BsubPc in a solid-state arrangement, available through the CCDC database as PHTLBC02-1052234.…”