Elucidation of the Structure–Property Relationship of p-Type Organic Semiconductors through Rapid Library Construction via a One-Pot, Suzuki–Miyaura Coupling Reaction

Abstract

The elucidation of the structure-property relationship is an important issue in the development of organic electronics. Combinatorial synthesis and the evaluation of systematically modified compounds is a powerful tool in the work of elucidating structure-property relationships. In this manuscript, D-π-A structure, 32 p-type organic semiconductors were rapidly synthesized via a one-pot, Suzuki-Miyaura coupling with subsequent Knoevenagel condensation. Evaluation of the solubility and photovoltaic properties of the prepared compounds revealed that the measured solubility was strongly correlated with the solubility parameter (SP), as reported by Fedors. In addition, the SPs were correlated with the Jsc of thin-film organic solar cells prepared using synthesized compounds. Among the evaluated photovoltaic properties of the solar cells, Jsc and Voc had strong correlations with the photoconversion efficiency (PCE).

Facile, One‐Step Synthesis of 5‐Substituted Thieno[3,4‐c]pyrrole‐4,6‐dione by Palladium‐Catalyzed Carbonylative Amidation

“…The use of inorganic bases such as K 3 PO 4 and CaH 2 afforded a substantial amount of intermediate 3 (Entries 1 and 2). The optimization of the combination of catalysts and ligands (Entries [10][11][12] revealed that the combination of Pd(OAc) 2 / [(tBu 3 P)H]BF 4 afforded the best result (46 %), as shown in Entry 12. The use of toluene as a solvent was important.…”

“…More diluted conditions (0.125 m) resulted in a decrease of yield (Entry 3) and recovery of substrate 1. 2-Thio-phenecarbaldehydes are important structural components of dyes for dye-sensitized solar cells, [9b,9d,14] as well as for the use with drug candidates, [8c] and for use as organic ptype semiconductors, [10] because the aldehyde group offers opportunities for further chemical modifications. In this case, substrate 1 was recovered probably due to the slow oxidative addition of 1 to the Pd 0 species that was coordinated by multiple CO molecules.…”

“…Approaches for the synthesis of cyclic imides. [7a,7e] We have synthesized bioactive compounds, [8] dyes, [9] and p-type semiconductors [10] for solar cells by sequential palladium-catalyzed cross-coupling reactions. [7] However, the carbonylative amidation of five-membered di-haloaryl rings have rarely been studied despite the usefulness of the products -as far as we could ascertain, only two reports have been published, as shown in Scheme 1 (c) and (d).…”

Convenient synthesis of EDOT-based dyes by CH-activation and their application as dyes in dye-sensitized solar cells

“…In the longer term, our protocols could be further extended to provide a combinatorial-like approach to allow the rapid screening of the structure-property relationships of diverse libraries of dyes. 35,45 Interestingly, a comparison of device performance data of the three dyes shows that the N,N-dimethyaniline moiety produces devices with comparable efficiency to analogous sensitizers containing a N,N-dimethylaniline donor unit attached to the EDOT unit via an acetylene bridge or dyes containing more complicated indoline or triphenylamine donor units reported in the literature. 26,28,37 A substantial improvement in device performance (8.2%) was reported for a triphenylamine containing EDOT sensitizer but this is due to a modication of the acceptor unit in the dye.…”

Facile synthesis of unsymmetrical and π-extended furan-diketopyrrolopyrrole derivatives through C–H direct (hetero)arylation using a heterogeneous catalyst system

“…[1][2][3][4] Traditionally, these carbon-hydrogen (C-H) DHA methods are catalyzed by soluble homogeneous palladium catalyst systems, which have the drawbacks of lower selectively, sensitivity to air, need for high temperature, and high-levels of residual palladium contamination in the resultant material. 5,6 In our group, we have recently reported on the synthesis of symmetrical small molecule-based semiconductors through a heterogeneous palladium (Pd) catalyzed DHA procedure.…”