An expedient synthesis of fused heteroacenes bearing a pyrrolo[3,2-b]pyrrole core

Abstract

Two linear fused heteroacenes bearing a pyrrolo[3,2-b]pyrrole core have been synthesized via a novel reductive ring closure methodology in three steps and in good overall yield. Preliminary OFET results showed that dinaphtho[2,3-b:2',3'-f]pyrrolo[3,2-b]pyrrole (DNPP) is a potential candidate for organic electronics.

The Influence of Structural Variations on the Heteroacenes Containing Dihydropyrrolo[3,2‐b]pyrrole Core on Their OFET Performances

“…We have reported a novel synthetic strategy for the synthesis of dihydropyrrolo[3,2‐ b ]pyrrole derivatives,, which enable us to make a series of heteroacenes bearing the dihydropyrrolo‐ [3,2‐ b ]pyrrole core, including DNPP and its isomer iso ‐DNPP , DQPP , in which two nitrogen atoms was introduced to replace the carbon atom, and tetra‐chlorinated DBPP, TClDBPP (Scheme ). Here we wish to report a systematical study on the OFET performance of these heteroacenes, which reveals the influence of the ring‐fusion pattern, heteroatom introduction, π‐conjugation length, and chlorine substitution on the crystallinity, orientation and morphology of the heteroacenes hence their OFET performance.…”

Design, Synthesis, and Versatile Processing of Indolo[3,2‐b]indole‐Based π‐Conjugated Molecules for High‐Performance Organic Field‐Effect Transistors

“…IDID thus allows symmetrical structural derivatization in ( N , N -), (2,7-), and (3,8-) positions affording diverse opportunities to control their π-conjugation and solubility with higher fl exibility than the case of pentacene and heptacene analogues (e.g., indolocarbazole, and heptazole). [23][24][25] In case of OFET application, only one report of vacuum-deposited (VD) device was made using underivatized IDID core which showed rather low mobility value of ≈1.0 × 10 −3 cm 2 V −1 s −1 ; [ 25 ] we thus believe it is worthwhile to tailor molecular structures of IDID with an aim to realize high-performance and versatilely processable organic semiconductors via precise comprehension of structure-property relationship. [23][24][25] In case of OFET application, only one report of vacuum-deposited (VD) device was made using underivatized IDID core which showed rather low mobility value of ≈1.0 × 10 −3 cm 2 V −1 s −1 ; [ 25 ] we thus believe it is worthwhile to tailor molecular structures of IDID with an aim to realize high-performance and versatilely processable organic semiconductors via precise comprehension of structure-property relationship.…”

1,4‐Dihydropyrrolo[3,2‐b]pyrrole and Its π‐Expanded Analogues

“…Their reaction with phenylhydrazine gave substituted indoloA C H T U N G T R E N N U N G [3, 2-b]indoles. [50] Self-condensation of methyl 2-aminobenzoate (49) The same methodology was utilized by the same authors in the first synthesis of p-expand- [50] Self-condensation of methyl 2-aminobenzoate (49) The same methodology was utilized by the same authors in the first synthesis of p-expand-…”

“…The value of E HOMO for 54 is significantly higher than the values for ladder distyrylbenzenes with silicon and chalcogen bridges, [63] for S,N-heterohexacenes reported by Bäuerle and co-workers, [64] and for dibenzoindoloA C H T U N G T R E N N U N G [3, 2-b]carbazole. [50,65] 5. [50,65] 5.…”

“…For the preparation of parent 1,4-dihydropyrroloA C H T U N G T R E N N U N G [3,2-b]pyrroles, the Hemetsberger [2,5] and our [11] methods seem to be the most general and straightforward ones. [50,54] These synthetic advancements, combined with record high electron density, close to unity fluorescence quantum yields, strong fluorescence in the solid state, nonlinear optical properties, and encouraging preliminary OFET results, make 1,4-dihydropyrroloA C H T U N G T R E N N U N G [3,2-b]pyrroles and p-expanded analogues the molecules of choice for photonics of the next decade. Needless to say, thermal isomerization of cis-triazatris-s-homobenzene is simply a scien-tific curiosity because the synthesis of the substrate is an achievement in itself.…”