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Generating a three-dimensional non-fullerene electron acceptor by combining inexpensive spiro[fluorene-9,9′-xanthene] and cyanopyridone functionalities
Materials Chemistry Frontiers ( IF 7 ) Pub Date : 2018-03-27 , DOI: 10.1039/c8qm00067k
Gajanan Kadam 1, 2, 3, 4, 5 , Anuradha Anuradha 6, 7, 8, 9 , Anubha Agarwal 9, 10, 11, 12 , Avinash Puyad 5, 13, 14 , Duong Duc La 6, 7, 8, 9 , Richard A. Evans 9, 15, 16 , Jingliang Li 9, 10, 11, 12 , Akhil Gupta 9, 10, 11, 12 , Sheshanath V. Bhosale 5, 17, 18
Affiliation  

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.

中文翻译:

通过结合廉价的螺[芴-9,9'-x吨]和氰基吡啶酮官能团生成三维非富勒烯电子受体

通过廉价合成的结构片段,螺[芴-9,9'-x吨](又称低成本螺)和氰基吡啶酮的组合,我们在此报告了一种新型的三维小分子非富勒烯电子受体,( 5 ž,5' ž,5'' é,5''' ë)-5,5-',5'',5''' - ((((小号) -螺[芴-9,9'-呫吨] -2,2',7,7'-四基)四(噻吩-5,2-二基)四(甲叉基)四(4-甲基-1-辛基-2,6-二氧-1,2, 5,6-四氢吡啶-3-甲腈] [ A1 ],合成后可用于溶液处理的本体异质结器件中,并通过质子和碳NMR光谱学以及元素分析对其进行了全面表征。A1通过使用Knoevenagel缩合反应的简便的合成方法合成了氯乙烯,发现其在各种常见的加工溶剂如氯仿和邻二氯苯中高度可溶。由于其设想的设计,A1显示出有希望的光电性能,并且能级互补了常规供体聚合物聚(3-己基噻吩)[P3HT]和聚({4,8-双[(2-乙基己基)氧基]苯并[ 1,2- b:4,5 - b ']二噻吩-2,6-二基} {3-氟-2-[(2-乙基己基)羰基]-噻吩并[3,4- b ]噻吩基})[PTB7 ]。鉴于其能量水平,溶解度和出色的成膜能力,A1用于体异质结器件中的N-半导体用作n型半导体组件。器件性能[D:A 1:1.2 = 5.84%(P3HT); 7.21%(PTB7)]验证了A1作为有效的非富勒烯受体的设计和使用。
更新日期:2018-05-31
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