Diindole[3,2- b :4,5- b ′]pyrrole as a chromophore containing three successively fused pyrroles: synthesis, optoelectronic properties and π-functionalization

Serendipitous Formation of Semiconducting Semi-Nindigo Indigoid by the Degradation of Diindolopyrrole

“…11-Phenyl-6,11-dihydro-5 H -pyrrolo­[3,2- b :4,5- b ′]­diindole (1) was synthesized; its NMR spectral data matched that reported in literature.…”

“…The dye 2 was discovered serendipitously when a blue compound was formed upon evaporation of 1 in dioxane (Figure S1). The effect has not been observed in other solvents, such as THF, DCM, diethyl ether, or acetone.…”

Band gap engineering of donor–acceptor co-crystals by complementary two-point hydrogen bonding

“…Based on these considerations, two diindolopyrroles 1 and 2 (Scheme 2) were synthesized as H-bonding p-electron donors, following a published procedure. 41 N-Alkylated derivative 1 0 was also synthesized as a control compound lacking H-bonding functionality. Cyclic voltammograms of 1, 2, and 1 0 exhibit reversible oxidations at 0.00 V, À0.10 V and À0.19 V ferrocene (Fc) (Fig.…”

Synthesis of Linearly Fused Benzodipyrrole Based Organic Materials

“…The synthesis starts from N -alkylated or N -arylated pyrrole 193 that is coupled with two molecules of 2-bromo-nitrobenzene 194 to form 195 in moderate yield (38%–50%). Then, a double Cadogan ring closure (48%–53%) is performed to obtain 196 , which is alkylated twice in 65%–87% yield to obtain the final compound 197 (Scheme 52) [103].…”