Thieno[3,2-b]pyrrolo Donor Fused with Benzothiadiazolo, Benzoselenadiazolo and Quinoxalino Acceptors: Synthesis, Characterization, and Molecular Properties

Abstract

Nitrogen-bridged donor-acceptor multifused dithienopyrrolobenzothiadiazole (DTPBT) and dibenzothiadiazolopyrrolothiophene (DBTPT) were successfully synthesized by intramolecular Cadogan annulation. The electron-deficient benzothiadiazole unit in DTPBT can be converted to benzoselenadiazole and quinoxaline moieties through reduction/cyclization to generate dithienopyrrolobenzoselenadiazole (DTPBSe) and dithienopyrroloquinoxaline (DTPQX), respectively. The nitrogen atoms function as the bridges for covalent planarization to induce intermolecular interaction and intramolecular charge transfer.

Triazole‐fused indolo[2,3‐a]carbazoles: synthesis, structures, and properties

“…[ 17,18 ] We have recently reported structure‐property relationship in oxadiazole‐, thiadiazole‐, and selenadiazole‐fused ICs. [ 19 ] Analogous di(furo/thieno/seleno‐pyrrolo)‐benzothiadiazole, [ 15,20–24 ] benzoselenadiazole, [ 20 ] and benzotriazole [ 25,26 ] have been synthesized using Cadogan cyclization [ 27 ] as a key step and incorporated into the conjugated copolymers, dyes, ladder conjugated polymers, [ 28 ] and non‐fullerene acceptors for organic photovoltaics. [ 29 ]…”

Incorporating an Alternating Donor–Acceptor Structure into a Ladder Polymer Backbone

“…Dibrominated BTDTP (BTDTP-Br)was synthesized according to the literature. [12] Thed iboronic ester-substituted terephthalophenone derivative C(O)P-BPin (BPin = pinacolato boron) was prepared from the corresponding dibrominated compound C(O)P-Br [3,6] in aM iyaura borylation. [13] Thes ynthesis of C(O)P-Br follows ak nown procedure.…”

Synthesis of a thiophene-fused isoindigo derivative: a potential building block for organic semiconductors

“…32 This band shows an intramolecular charge-transfer character, since HOMO of the isoindigo is much more delocalized throughout the whole molecule, while the LUMO is more localized on the central rings. A strengthened absorption of C8-TII and C8-BII implies a strengthened intramolecular charge-transfer process 33 that occurs in them. This might be due to the aromatic/heteroaromatic rings fused onto the isoindigo core in C8-TII and C8-BII.…”