Isoindole-BODIPY dyes as red to near-infrared fluorophores.
Isoindole-BODIPY dyes as red to near-infrared fluorophores.
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DOI：
10.1002/chem.201200398
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发表时间：
2012-05
期刊：
影响因子：
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通讯作者：
Changjiang Yu;Yajun Xu;Lijuan Jiao;Jinyuan Zhou;Zhaoyun Wang;Erhong Hao
中科院分区：
文献类型：
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作者：
Changjiang Yu;Yajun Xu;Lijuan Jiao;Jinyuan Zhou;Zhaoyun Wang;Erhong Hao
在红色或近红外(NIR)区域发射的明亮荧光染料，[1，2]由于其最大限度地穿透皮肤和组织，散射最小而被首选用于生物成像，[3]最近引起了广泛的研究兴趣，作为新的标准发光染料，用于生物分子和其他应用。[4]在少数可用的深红色和近红外(NIR)荧光团中，许多存在某些光学特性不足的问题，如荧光量子产率低或光稳定性差。因此，人们一直致力于远红外和近红外有机荧光团的制备和评价。[5]二吡咯亚硼(BODIPY)染料(图1)因其优异的性质而备受关注，如大的吸收消光系数、尖锐的荧光发射、高的荧光量子产率和高光物理稳定性。在远红区或近红外区发射BODIPY的方法有多种：1)可旋转部分的硬化；[7]2)8碳原子被氮原子取代形成氮杂-BODIPY染料；[8]3)通过引入芳基、乙烯基、苯乙烯基和芳乙炔取代基[9]和通过Knovenagel缩合或过渡金属催化的交叉偶联反应引入“推-拉”基序[10]来扩展π的共轭；和4)通过将芳基部分融合到吡咯单元来扩展π共轭。[11，12]在这里，我们报道了一种简单的一锅法合成3-吡咯/吲哚取代的异吲哚-联苯二异氰酸酯染料，其苯环融合在联苯二异丙酮的1，2-位上(方案1)。这些合成的异吲哚-BODIPY染料表现出很强的吸收和发射性能，可以很容易地从光谱的红色区域调谐到近红外区域。此外，于春秋，徐勇，焦立中教授，周军，王振中教授，郝E.教授，安徽师范大学化学与材料科学学院分子基材料科学安徽实验室，芜湖，241000(公关中国)电子邮件：jiao421@mail。阿努。艾杜。Cn haoehong@mail。阿努。艾杜。CN本文的支持信息可在万维网上的http://dx.下获得多伊。Org/10.1002/chem.201200398。
Bright fluorescent dyes emitting in the red or near-infrared (NIR) region,[1, 2] which is preferred for biological imaging due to the maximum light penetration through skin and tissue with minimum scattering,[3] have lately attracted wide research interest as new standard luminescent dyes, fluorescent probes for biomolecules and other applications.[4] Among the few available deep-red and NIR fluorophores, many suffer from certain insufficient optical characteristics, such as low fluorescence quantum yields or poor photostability. Thus, continuous research efforts have been devoted to the preparation and evaluation of new families of far-red and NIR organic fluorophores.[5] Boron dipyrromethene (BODIPY) dyes (Figure 1) have received much attention due to their outstanding properties, such as large absorption extinction coefficients, sharp fluorescence emissions, high fluorescence quantum yields and high photophysical stability.[6] However, the absorption and emission wavelengths for classical BODIPY chromophore centre at 470–530 nm. Various approaches have been developed for BODIPYs emitting in far-red or NIR region: 1) rigidification of rotatable moieties;[7] 2) replacement of the 8-carbon atom by a nitrogen atom to form aza-BODIPY dyes;[8] 3) extension of the π conjugation by introduction of aryl, vinyl, styryl and arylethynyl substituents [9] and introduction of the “push–pull” motif [10] through Knoevenagel condensation or transition metal-catalyzed cross coupling reaction; and 4) the extension of the π conjugation by the fusion of aryl moieties to the pyrrole unit.[11, 12] Herein, we report a facile one-pot synthesis of 3-pyrrole/indole substituted isoindole-BODIPY dyes, which have a benzene ring fused to the 1, 2-positions of the BODIPY core (Scheme 1). These resultant isoindole-BODIPY dyes exhibit strong absorption and emission properties that could be easily tuned from red to NIR region of the spectra. In addition, the fluo-[a] C. Yu, Y. Xu, Prof. Dr. L. Jiao, J. Zhou, Z. Wang, Prof. Dr. E. Hao Laboratory of Functional Molecular Solids, Ministry of Education Anhui Laboratory of Molecule-Based Materials School of Chemistry and Materials Science Anhui Normal University, Wuhu, 241000 (PR China) E-mail: jiao421@ mail. ahnu. edu. cn haoehong@ mail. ahnu. edu. cn Supporting information for this article is available on the WWW under http://dx. doi. org/10.1002/chem. 201200398.