Azadipyrromethene-based near-IR dyes with styryl substituents at the pyrrolic positions for organic photovoltaic applications

Azadipyrromethene-based near-IR dyes with styryl substituents at the pyrrolic positions for organic photovoltaic applications
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用于有机光伏应用的吡咯位置带有苯乙烯基取代基的氮杂二吡咯亚甲基近红外染料

DOI:
10.1016/j.dyepig.2019.04.067
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发表时间:
2019
期刊:
影响因子:
4.5
通讯作者:
Sauvé, Geneviève
Sauvé, Geneviève
中科院分区:
材料科学2区
文献类型:
--
作者:
Fernando, Roshan;Pejić, Sandra;Thomsen, Anna;Wang, Chunlai;Sauvé, Geneviève

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氮杂二吡咯亚甲基染料是开发近红外染料的有吸引力的构件,其应用范围从生物传感、光动力治疗和太阳能转换。特别是,Zn(II)双(2,8-二苯基乙炔基1,3,7,9-四苯基氮杂二吡咯亚甲基)配合物是很有前途的n型非富勒烯电子受体的有机光致发光。此处,苯乙炔基吡咯取代基中的三键被双键替代。UV-Vis吸收光谱没有显著差异,表明双键和三键都类似地延长了ADP的缀合。有趣的是,带有苯乙烯基取代基的Zn(II)配合物(Zn(WS 6)2)在近红外区有发射,λ max为773 nm。BF ~(2+)螯合物在近红外区也有发射,λ max为815 nm,但发射很弱。循环伏安法显示,双键化合物比未取代的ADP类似物更容易氧化,而不像三键化合物更容易还原。在有机光致发光中,Zn(WS 6)2的表现不如Zn(WS 3)2类似物,当与P3 HT混合时显示出不利的薄膜形态,并且SCLC的混合电子迁移率为2 × 10− 8 cm 2 V − 1 s − 1,而纯薄膜为1 × 10− 7 cm 2 V − 1 s − 1。Zn(WS 6)2在纯膜中的空穴迁移率为6 × 10− 5cm 2 V − 1 s −1,高于其电子迁移率,表明其也是p型材料。进一步的工作,在寻找合适的n-型聚合物受体,需要证实这一假设。因此,在吡咯位置使用三键比双键更适合于基于ADP染料的n型材料的开发。
Azadipyrromethene dyes are attractive building blocks for the development of near-IR dyes, with applications ranging from biosensing, photodynamic therapy and solar energy conversion. In particular, Zn(II)bis(2,8-diphenylethynyl 1,3,7,9 tetraphenylazadipyrromethene) complexes are promisingn-type non-fullerene electron acceptors for organic photovoltaics. Here, the triple bond in phenylethynyl pyrrolic substituents is replaced with a double bond. The UV–Vis absorption spectra were not significantly different, indicating that both the double and triple bond similarly extend the conjugation of ADP. Interestingly, the Zn(II) complex with styryl substituents (Zn(WS6)2) showed emission in the near IR, with aλmaxof 773 nm. The BF2+chelate also emitted in the near IR with aλmaxof 815 nm, but the emission was very weak. Cyclic voltammetry revealed that double bond compounds were easier to oxidize than un-substituted ADP analogues, and unlike with triple bond, were not easier to reduce. In organic photovoltaics, the Zn(WS6)2did not perform as well as the Zn(WS3)2analogue, showing unfavorable film morphology when blended with P3HT and low blend electron mobility of 2 × 10−8cm2V−1s−1by SCLC, compared to 1 × 10−7cm2V−1s−1in neat film. The hole mobility of Zn(WS6)2in neat films is 6 × 10−5cm2V−1s−1, higher than its electron mobility, suggesting its potential as p-type material as well. Further work in finding an appropriate n-type polymer acceptor is required to confirm this hypothesis. Using a triple bond at the pyrrolic positions is therefore better than a double bond for the development ofn-type materials based on ADP dyes.
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DOI: 10.1021/om900552e
发表时间: 2009
期刊: Organometallics
影响因子: 2.8
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影响因子: 2.3
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