Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,90-xanthene] and cyanopyridone functionalities

Kadam, G, Anuradha, A, Agarwa, A, Puyad, A, La, D, Evans, R, Li, J, Gupta, A and Bhosale, S 2018, 'Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,90-xanthene] and cyanopyridone functionalities', Materials Chemistry Frontiers, vol. 2, no. 6, pp. 1090-1096.


Document type: Journal Article
Collection: Journal Articles

Title Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,90-xanthene] and cyanopyridone functionalities
Author(s) Kadam, G
Anuradha, A
Agarwa, A
Puyad, A
La, D
Evans, R
Li, J
Gupta, A
Bhosale, S
Year 2018
Journal name Materials Chemistry Frontiers
Volume number 2
Issue number 6
Start page 1090
End page 1096
Total pages 7
Publisher Royal Society of Chemistry
Abstract Through the combination of cheaply synthesized structural fragments, spiro[fluorene-9,90-xanthene] - otherwise termed low-cost spiro - and cyanopyridone, herein we report a new, three-dimensional, small molecule non-fullerene electron acceptor, (5Z,50Z,500E,0 00E)-5,50,500,50 00-((((S)-spiro[fluorene-9,90-xanthene]-2,20,7,70-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-b0]-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.
Subject Synthesis of Materials
DOI - identifier 10.1039/c8qm00067k
Copyright notice © 2018 Royal Society of Chemistry. All rights reserved.
ISSN 2052-1537
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