Eco-friendly direct (hetero)-arylation polymerization: scope and limitation

Nguyễn

et al. 2019

Polymer International

In this research, new donor–acceptor (D‐A) photovoltaic polymers were synthesized from dithieno[3,2‐b:2′,3′‐d]pyrrole electron donor derivatives, including N‐benzoyldithieno[3,2‐b:2′,3′‐d]pyrrole and N‐(4‐hexylbenzoyl)dithieno[3,2‐b:2′,3′‐d]pyrrole, in combination with the electron deficient unit 2,5‐bis(2‐ethylhexyl)‐3,6‐di(thiophen‐2‐yl)‐2,5‐dihydropyrrolo[3,4‐c]pyrrole‐1,4‐dione via direct (hetero)arylation polymerization. The D‐A conjugated polymers obtained were characterized via 1H NMR, gel permeation chromatography, Fourier transform infrared spectroscopy, DSC, XRD, photoluminescence and UV–visible methods. In addition, these D‐A polymers were used as activated layers in bilayer and bulk heterojunction structures for the fabrication of organic photovoltaic cells. © 2019 Society of Chemical Industry

Section: Introductionmentioning

confidence: 99%

Direct (hetero)arylation polymerization for the synthesis of donor–acceptor conjugated polymers based on N‐benzoyldithieno [3,2‐b:2′,3′‐d]pyrrole and diketopyrrolopyrrole toward organic photovoltaic cell application

Nguyễn

et al. 2019

Polymer International

Macro Chemistry & Physics

“…Although high‐performing materials advance and motivate the field, the development of low‐cost synthetic routes for organic electronic materials is a critical consideration for the commercial application of OPV technologies . Recently, direct arylation polymerization (DArP) has emerged as a new technique for the preparation of semiconducting polymers . In comparison with traditional Stille coupling methods, DArP is highly efficient, allowing several synthetic steps to be circumvented.…”

Section: Introductionmentioning

confidence: 99%

Exploration of the Direct Arylation Polymerization Method for the Practical Application of Conjugated Materials: Synthetic Scale‐Up, Solar Cell Performance, and Cost Analyses

Pappenfus

Almyahi

Cooling

et al. 2018

This study reports the scalability of direct arylation polymerization (DArP) batch reactions for the preparation of poly(3‐hexylthiophene) (P3HT) using the Herrmann–Beller catalyst combined with a tertiary phosphine in the green solvent 2‐methyltetrahydrofuran on scales ranging from 0.5 to 10 g. The physical properties of these DArP polymers are compared to those resulting from P3HT prepared via Grignard metathesis (GRIM) on a 130 g scale. Both DArP and GRIM methods are found to produce highly regioregular polymers with no evidence of β‐defects and the polymers are found to exhibit comparable device performance as donor materials in bulk heterojunction organic solar cells. Purification studies coupled with device measurements highlight the necessity to carefully address the presence of impurities in materials produced from large‐scale DArP batch reactions. Economic analyses reveal that the cost involved in the preparation of P3HT via DArP or GRIM procedures are comparable per gram of product and show that the most expensive component is unique for each method.

“…This has rendered many top performing materials expensive and not suitable for solar cell mass production [ 4 , 5 , 6 , 7 ]. Hence, to avoid this cryptic situation, the direct (hetero)arylation (DHA) appears to be method of choice, from the chemist point of view, to afford the next generation of π-conjugated materials [ 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 ]. The latter indeed offers several practical advantages such as ( i ) a simplified and shortened synthetic route; ( ii ) a better stability of the monomers; ( iii ) the prevention of metal-substituted terminal groups; ( iv ) a lower environmental impact, since organometallic transmetallation derivatives are no longer necessary and ( v ) the unique opportunity of affording new compounds that cannot be achieved with the traditional methods.…”

Section: Introductionmentioning

confidence: 99%

Direct (Hetero)Arylation Polymerization of a Spirobifluorene and a Dithienyl-Diketopyrrolopyrrole Derivative: New Donor Polymers for Organic Solar Cells

et al. 2018

Self Cite

The synthesis and preliminary evaluation as donor material for organic photovoltaics of the poly(diketopyrrolopyrrole-spirobifluorene) (PDPPSBF) is reported herein. Prepared via homogeneous and heterogeneous direct (hetero)arylation polymerization (DHAP), through the use of different catalytic systems, conjugated polymers with comparable molecular weights were obtained. The polymers exhibited strong optical absorption out to 700 nm as thin-films and had appropriate electronic energy levels for use as a donor with PC70BM. Bulk heterojunction solar cells were fabricated giving power conversion efficiencies above 4%. These results reveal the potential of such polymers prepared in only three steps from affordable and commercially available starting materials.