IRFP: Boron-Containing Organic Donor-Acceptor Scaffolds: Chemoresponsive Optoelectronic Materials

国际研究奖学金计划使美国科学家和工程师能够在国外进行9到24个月的研究。该项目的奖项提供了联合研究的机会，并提供了使用国外独特或互补的设施、专业知识和实验条件的机会。该奖项将资助Aaron D.Finke博士与Francois Diederich博士在瑞士苏黎世的瑞士苏黎世理工学院合作的为期24个月的研究奖学金。拟议的研究涉及在一类新型有机发色团中掺入硼的影响。[2 2]以富电子的烯烃和贫电子的烯烃为原料的环加成/环逆转化学因其合成简单、原子经济、生成复杂等优点而成为制备小尺寸发色团的理想方法。这些生色团含有富电子的苯胺和贫电子的四氰基丁二烯，由于强烈的电荷转移行为，通常是高色的，表现出与目前已知的最好的有机电子受体相当的还原电位。它们还具有高的非线性光学活性，这已被用于光波导器件中。关于不同官能团的掺入和作用来调节这些生色团的光电性质的研究一直是有限的。在共轭有机体系中加入接受电子的硼单元应该允许更强的接受电子的性质，并引入一种新的能力来更精细地调节这些材料的接受电子的行为，从而改变其光学和电化学性质。一旦对含有机硼的“超受体”有了更深入的了解，这项拟议的研究将寻求利用含有机硼官能团的化学响应性应用于新的化学传感应用。这项工作将加深我们对强有机受体材料中接受电子基团的影响的理解。在共轭有机材料中加入主族元素将进一步使目前可用的有机电子材料类型多样化。硼的高可获得性、低成本和低毒性使其具有吸引力，可以为目前依赖昂贵和/或有毒金属的设备开发更环保的材料。此外，将有机硼烷等具有化学响应性的部分加入到共轭体系中，应允许采用新的方法来检测环境污染物，如公共卫生应用中的氟化物。

The International Research Fellowship Program enables U.S. scientists and engineers to conduct nine to twenty-four months of research abroad. The program's awards provide opportunities for joint research, and the use of unique or complementary facilities, expertise and experimental conditions abroad. This award will support a twenty-four-month research fellowship by Dr. Aaron D. Finke to work with Dr. Francois Diederich at the ETH-Zurich in Zurich, Switzerland.The proposed research concerns the effects of boron incorporation in a novel class of organic chromophores. [2+2] cycloaddition/cycloreversion chemistry with electron-rich alkynes and electron-poor olefins is an ideal method for preparation of chromophores of small size because of its synthetic facility, atom economy, and generation of complexity. These chromophores, which contain an electron-rich aniline and electron-poor tetracyanobutadiene, are typically highly-colored due to strong charge-transfer behavior, and exhibit reduction potentials on par with the best organic electron-acceptors currently known. They also possess high nonlinear optical activity which has been exploited in devices such as optical waveguides. Studies on the incorporation and effects of different functional groups to modulate the optoelectronic properties of these chromophores have been limited. The addition of electron-accepting boron moieties into conjugated organic systems should allow for stronger electron-accepting properties as well as introduce a new ability to more finely "tune" the electron-accepting behavior, and thus the optical and electrochemical properties, of these materials. Once a greater understanding of organoboron-containing "super-acceptors" is gained, the proposed research will seek to exploit the chemoresponsive nature of organoboron-containing functional groups for novel chemical sensing applications. This work will enhance our understanding of the effects of electron-accepting groups in strong organic acceptor materials. Main-group element incorporation into conjugated organic materials will futher diversify the types of organic electronic materials that are currently available. Boron's high availability, low cost, and low toxicity make it attractive for the development of "greener" materials for devices that currently rely on expensive and/or toxic metals. Furthermore, the incorporation of chemically-responsive moieties such as organoboranes into conjugated systems should allow for new approaches toward systems for the detection of environmental contaminants such as fluoride for public health applications.