Issue 56, 2019

High-yielding Pd2(dba)3·C6H6-based four-fold Sonogashira coupling with selenophene-conjugated magnesium tetraethynylporphyrin for organic solar cells

Abstract

A catalytic system using Pd2(dba)3·(C6H6)/PPh3/CuI for Sonogashira coupling was demonstrated to synthesize a selenophene-conjugated magnesium tetraethynylporphyrin Mg-TEP-(Se-DPP)4 (2a). The catalytic system enabled four-fold cross-coupling of the four terminal alkynes of magnesium tetraethynylporphyrin with bromoselenophene-tethered diketopyrrolopyrroles (DPPs) to produce the desired star-shaped 2a in 80% yield. This molecule shows higher solubility in organic solvents, more efficient visible and near-infrared region absorption, and a narrower band gap compared with reference thiophene-conjugated congeners. Two strategies, namely, selenium substitution and end-capping, were investigated to optimize bulk heterojunction structures in the active layers of organic solar cells. The optimized device based on 2a:PC61BM exhibited the highest PCE of 6.09% among the tested devices after solvent vapor annealing, owing to efficient exciton dissociation, balanced carrier mobility, and suppressed carrier recombination in the film's ordered morphology.

Graphical abstract: High-yielding Pd2(dba)3·C6H6-based four-fold Sonogashira coupling with selenophene-conjugated magnesium tetraethynylporphyrin for organic solar cells

Supplementary files

Article information

Article type
Paper
Submitted
14 Sep 2019
Accepted
25 Sep 2019
First published
11 Oct 2019
This article is Open Access
Creative Commons BY license

RSC Adv., 2019,9, 32562-32572

High-yielding Pd2(dba)3·C6H6-based four-fold Sonogashira coupling with selenophene-conjugated magnesium tetraethynylporphyrin for organic solar cells

H. Wang, T. Nakagawa, M. Zhang, K. Ogumi, S. Yang and Y. Matsuo, RSC Adv., 2019, 9, 32562 DOI: 10.1039/C9RA07393K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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