Two asymmetrical perylene diimide derivatives: Synthesis, optical-electrochemical properties and morphologies of self-assembly

Synthesis, optical properties and self-assemblies of three novel asymmetrical perylene diimides modified with functional hydrogen bonding groups at bay positions

“…The synthetic route of three PDIs is shown in Chart 1. Compounds 1–6 , 21–24 PDI-0 25 and PDI-Br 26 were synthesized according to the literature. Intermediate PDI-Br was prepared using a bromination reaction with bromine and mixtures of regioisomeric 1,7- and 1,6-dibromoperylene diimides (4 : 1) were obtained.…”

“…7). The first onset reduction potential ( E onset red ) values of PDI-NH 2 , PDI-OH and PDI-COOH are identical at −0.55 V, and the lowest unoccupied molecular orbital (LUMO) energy levels of the three PDIs are deduced from E onset red according to the equation E LUMO = −( E onset red − E Fc + 4.8) eV, 25 where the value of the oxidation potential of ferrocene ( E Fc ) vs. Ag/AgCl is 0.36 V (Fig. S18, ESI†).…”

“…The LUMO energy levels of the three PDIs are −3.89 eV. The absorption edges ( λ onset ) of PDI-NH 2 , PDI-OH and PDI-COOH are 663 nm, 596 nm and 573 nm, respectively, and their E g opt values are estimated to be 1.87 eV, 2.08 eV and 2.16 eV, respectively, according to E g opt = 1240/ λ onset 25 from the λ onset values in CH 2 Cl 2 (Fig. S19, ESI†).…”

“…From this value, the HOMO energies of PDI-NH 2 , PDI-OH and PDI-COOH are estimated as −5.76 eV, −5.97 eV and −6.05 eV using the equation: E HOMO = E LUMO − E g opt . 25 The low LUMO energy levels show stable electron-deficient properties as strong organic acceptors, which could find applications in optoelectronic devices like solar cells.…”

Alkynyl BODIPY-Core Bridged Perylene Diimide Star-Shaped Nonfullerene Acceptors for Efficient Polymer Solar Cells

“…Two compounds showed two characteristic reduction peaks. The first reduction potentials for BDP-3PDI and BDP-4PDI with an identical value at −0.77 V can be assigned to electrondeficient PDI moiety reduction, 68,69 while another reduction one around −1.11 V for BDP-3PDI and −1.01 V for BDP-4PDI corresponds to the reduction of the BODIPY-based reduction. 44 BDP-3PDI shows two oxidation potentials at 1.22 and 1.54 V, and BDP-4PDI displays three oxidation potentials at 1.02, 1.52, and 1.74 V, all of which are ascribed to the oxidation of the BODIPY core.…”