スクワライン染料の固体構造,キャリアモビリティ,およびバルクヘテロジャンクション太陽電池の効率性に対するアルキル対アルケニル置換剤の有意な効果
Diego Bagnis1, Luca Beverina, Hui Huang
1Department of Chemistry and the Argonne-Northwestern Solar Energy Research Center, Northwestern University, Evanston, Illinois 60208, USA.
Journal of the American Chemical Society
|March 9, 2010
まとめ
有機太陽電池のための2つの新しいスクワレイン染料の導入. ヘクセニル置換染料は,電荷輸送と電力変換効率 (PCE) を著しく向上させ,溶液処理デバイスでは2%以上のPCEを達成します.
科学分野:
- マテリアルサイエンス 材料科学
- オーガニック・エレクトロニクス
- フォトボルトイカは,太陽光発電です.
背景:
- スクワライン染料は,太陽電池アプリケーションのための有機半導体として有望です.
- 分子構造の最適化は,電荷輸送とデバイスの性能を改善するための鍵です.
研究 の 目的:
- 異なるサイドチェーン (n-ヘキシル対n-ヘクセニル) を有する2つの新しいスクワライン染料を合成し,特徴づけること.
- サイドチェーンの変更が固体包装,電荷輸送,有機光伏 (OPV) の性能に与える影響を調査する.
主な方法:
- n-ヘキシルおよびn-ヘキシル置換剤を用いたスクワライン染料の合成.
- 合成された染料を用いた大量ヘテロ結合 (BHJ) 有機太陽電池の製造.
- 薄膜形態の特徴,電荷輸送特性 (穴の移動性),およびデバイス性能 (パワー変換効率 - PCE).
主要な成果:
- n-ヘクセニル置換のスクワライン染料 (スクワライン2) は,n-ヘクセニル誘導物 (スクワライン1) に比べて,よりコンパクトな固体構造を示した.
- スクワライン2の薄膜の穴の動きは,スクワライン1の5倍以上でした.
- スクワライン2をベースにしたBHJ OPV装置は,スクワライン1を使用した装置の2倍のパワー変換効率 (PCE) を達成した.
- PCEは,環境溶液加工装置で2%を超え,スクラインベースの太陽電池の重要な進歩を表しています.
結論:
- n-ヘクセニル鎖の末端の二重結合は,スクワライン染料の固体包装と電荷輸送に大きな影響を与える.
- 構造的変更は,たとえ些細なものであっても,OPVの性能を劇的に向上させることができます.
- これらの発見は,スクワライン化学に基づく高性能,溶液加工有機太陽電池の開発の道を開く.
関連する概念動画
Stability of Substituted Cyclohexanes
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
π Electron Effects on Chemical Shift: Overview
An applied magnetic field causes loosely bound π-electrons in organic molecules to circulate, producing a local or induced diamagnetic field over a large spatial volume. As the molecules tumble in solution, the field generated by π-electrons in spherical substituents results in a zero net field. However, the net field generated by π-electrons in non-spherical substituents is not zero. The effect of this induced field depends on the orientation of the molecule with respect to B0, resulting in...
Relative Stabilities of Alkenes
The relative stability of alkenes can be determined by comparing their heats of hydrogenation. The lower heat of hydrogenation indicates the more stable alkene. The three main factors determining the relative stability of alkenes are i) the number of substituents attached to the double-bond carbon atoms, ii) hyperconjugation, and iii) the stereochemistry of the double bond.
Electrophilic Addition to Alkynes: Halogenation
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
Isomerism in Alkenes
Alkenes like 1-butene and 2-butene exhibit constitutional isomerism, as they differ in the position of the double bond. Further, 2-butene exhibits stereoisomerism and exists as two distinct compounds differing in spatial arrangement.
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
An isomer is called cis-2-butene when the methyl groups are on the same side of the double bond, and the other stereoisomer, in which methyl groups are on the opposite side of the double bond, is called trans-2-butene. The cis and trans stereoisomers are not...
Inductive Effects on Chemical Shift: Overview
The protons in unsubstituted alkanes are strongly shielded with chemical shifts below 1.8 ppm. Methine, methylene, and methyl protons appear at approximately 1.7, 1.2 and 0.7 ppm, while the proton signal from methane appears at 0.23 ppm. An electronegative substituent, such as chlorine, withdraws the electron density from the protons, increasing their chemical shift. Progressive substitution of the hydrogens in methane by chlorine shifts the proton signals increasingly downfield, to 3.05 ppm in...


