Jump to main content
Jump to site search

Issue 6, 2018
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 09 Feb 2018, accepted on 27 Mar 2018 and first published on 27 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QM00067K
Citation: Mater. Chem. Front., 2018,2, 1090-1096
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements