Benzodipyrrolidones and Their Polymers

1,6-Naphthodipyrrolidone-based donor–acceptor polymers with low bandgap

“…P4 at 345 C. This behavior is similar to the polymers based on isoDPP [22], or BDP [16]. The DSC traces (Fig.…”

“…This phenomenon is similar to polymers based on BDP, which do not show any fluorescence [16], and isoDPP, which exhibit Ф values <0.8% [22,24].…”

“…From Fig. 2a, one can see that the UV/vis absorption maxima of M1 and M2 in dichloromethane are located at 567 nm, which is red-shifted by about 130 nm compared with 1,5-BDP [16], and 110 nm red-shifted compared with isoDPP [24]. The overwhelming red-shift of the absorption can be ascribed to the core extension of 1,6-NDP, which enlarges the p-electron system and thus favors the bathochromic shift.…”

“…1,6-Naphthodipyrrolidone (1,6-NDP) is an electrondeficient pigment, which exhibits a purple color, a maximum absorption of 567 nm, and quite high extinction coefficients in dichloromethane [21]. The molecular structure resembles diketopyrrolo [3,2-b]pyrrole (isoDPP) [22e25], and benzodipyrrolidone [16] (1,5-BDP, Scheme 1) except that the 1,6-NDP core is tetracyclic, whereas isoDPP and BDP are bi-and tricyclic, respectively. The additional benzene rings enlarge the p-conjugated system and lead to a red-shift of the UV/vis absorption of 131 and 109 nm with regard to isoDPP and 1,5-BDP.…”

Imide- and Amide-Functionalized Polymer Semiconductors

“…438 P357 and P358 ( Figure 52) were synthesized via Suzuki coupling, and showed good solubilities in organic solvents. The P357 and P358 band gaps derived from the absorption onsets were 1.90 and 1.68 eV, respectively, which indicate that BDPDP should be an effective acceptor for constructing narrow band-gap polymers.…”