Synthesis of annulated thiophene perylene bisimide analogues: their applications to bulk heterojunction organic solar cells

Abstract

Annulated thiophene perylene bisimides and their triphenyl-amine based oligomers have been synthesized. One of the oligomers FPTTPA has been demonstrated to be an efficient electron donor in bulk heterojunction (BHJ) organic solar cells, giving a power conversion efficiency of 1.42%.

Conjugated polymers based on modified benzo[1,2-b:4,5-b′]dithiophene and perylene diimide derivatives: Good optical properties and tunable electrochemical performance

“…Thus those polymers synthesized with DTCDI have a strong tendency to form π-π stacks. 16 Based on computational modeling, P(BDT-DTCDI) should has an highly coplanar backbone with negligible angle. This is a evident advantage versus P(BDT-PDI) and P(BDT-DTPDI), where sterically encumbered bay region leads to significant polymer backbone torsion (39.64-41.44 o ).…”

“…14,15 Recently, dithienocoronene diimide (DTCDI) based conjugated polymers were synthesized for organic semiconductors, organic solar cells and two-photon absorption (2PA) materials. [16][17][18][19][20] In 2011, two D-A-D small molecule donors were synthesized by Ko and co-workers, which were composed of DTCDI as acceptor, triphenylamine as donor, and bithiophene as bridge and used in organic solar cells with the highest power conversion efficiency (PCE) of 1.42%. 16 In 2012, Facchetti and co-workers synthesized a series of D-A conjugated polymers based on DTCDI and thiophene or bithiophene, which applied in ambipolar field-effect transistors with the highest electron mobilities with 0.30 cm 2 V -1 s -1 and the highest hole mobilities with 0.04 cm 2 V -1 s -1 .…”

“…[16][17][18][19][20] In 2011, two D-A-D small molecule donors were synthesized by Ko and co-workers, which were composed of DTCDI as acceptor, triphenylamine as donor, and bithiophene as bridge and used in organic solar cells with the highest power conversion efficiency (PCE) of 1.42%. 16 In 2012, Facchetti and co-workers synthesized a series of D-A conjugated polymers based on DTCDI and thiophene or bithiophene, which applied in ambipolar field-effect transistors with the highest electron mobilities with 0.30 cm 2 V -1 s -1 and the highest hole mobilities with 0.04 cm 2 V -1 s -1 . 17 In 2012, Zhan and coworkers reported the D-A conjugated polymer of DTCDI and porphyrin, which exhibited strong two-photon absorption (2PA) at telecommunication wavelengths with 2PA cross sections per repeat unit as high as 7809 GM at 1520 nm, 19 and in 2013, they synthesized four n-type low-bandgap conjugated polymers based on DTCDI core as electron-acceptor and different thiophene number from 0 to 3 as electron-acceptor, PT5TPA 21 as donor for organic solar cells, the highest PCE is 0.84%.…”

Ambipolar copolymer of dithienocoronenedi-imide and benzo(bis)thiadiazole with balanced hole and electron mobility

“…In 2012, Facchetti's group reported a copolymer embedding DTCDI as acceptor, which performs ambipolar charge transport characteristics with electron mobility of 0.30 cm 2 V À1 s À1 and hole mobility of 0.04 cm 2 V À1 s À1 [22]. A small molecule containing DTCDI for bulk heterojunction (BHJ) organic solar cell also performed with power conversion efficiency (PCE) of 1.42% [27]. Most recently, Müllen's group reported that a new copolymer with two kinds of acceptors exhibited balanced ambipolar charge transport, with hole and electron mobility up to 0.02 cm 2 V À1 s À1 [24].…”

“…In 2012, a polymer P(BTZ4T) (Scheme 1) based on BTZ and thiophenes exhibited hole mobility of 0.01 cm 2 V À1 s À1 and low band-gap. Recently, a new acceptor of dithienocoronenediimide (DTCDI) was reported [22,27]. DTCDI has a larger conjugate backbone than DPP and NDI and has relatively strong electron-drawing ability, which makes DTCDI a potential building block for application in OFET and OPV.…”