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Issue 6, 2018

Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,9′-xanthene] and cyanopyridone functionalities

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Abstract

Through the combination of cheaply synthesized structural fragments, spiro[fluorene-9,9′-xanthene] – otherwise termed low-cost spiro – and cyanopyridone, herein we report a new, three-dimensional, small molecule non-fullerene electron acceptor, (5Z,5′Z,5′′E,5′′′E)-5,5′,5′′,5′′′-((((S)-spiro[fluorene-9,9′-xanthene]-2,2′,7,7′-tetrayl)tetrakis(thiophene-5,2-diyl))tetrakis(methaneylylidene))tetrakis(4-methyl-1-octyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile) [A1], which was synthesized for use in solution-processable bulk-heterojunction devices and was fully characterized by proton and carbon NMR spectroscopies together with elemental analysis. A1 was synthesized by a facile synthetic methodology using a Knoevenagel condensation reaction and was found to be highly soluble in a variety of common processing solvents such as chloroform and o-dichlorobenzene. Owing to its envisioned design, A1 displayed promising optoelectronic properties, and energy levels complementing those of the conventional donor polymers poly(3-hexylthiophene) [P3HT] and poly({4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl}{3-fluoro-2-[(2-ethylhexyl)carbonyl]-thieno[3,4-b]thiophenediyl}) [PTB7]. Given its energy levels, solubility and excellent film forming capability, A1 was used in bulk-heterojunction devices as an n-type semiconducting component. The device performances [D :  A 1 : 1.2 = 5.84% (P3HT); 7.21% (PTB7)] validated the design and use of A1 as an efficient non-fullerene acceptor.

Graphical abstract: Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,9′-xanthene] and cyanopyridone functionalities

Supplementary files

Article information


Submitted
09 Feb 2018
Accepted
27 Mar 2018
First published
27 Mar 2018

Mater. Chem. Front., 2018,2, 1090-1096
Article type
Research Article
Author version available

Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,9′-xanthene] and cyanopyridone functionalities

G. Kadam, Anuradha, A. Agarwal, A. Puyad, D. D. La, R. A. Evans, J. Li, A. Gupta and S. V. Bhosale, Mater. Chem. Front., 2018, 2, 1090 DOI: 10.1039/C8QM00067K

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