Synthesis and Evaluation of Perylenebisimide-Derived Donor-Sigma-Acceptor Molecules as Electrical Rectifiers

轨道能级的Aviram-Ratner模型预测，供体σ-受体（D-？- A）分子将只在一个方向上通过电子，即D-？-分子应该能整流。在这个项目中，一类新的材料，将二萘嵌苯双（二甲酰亚胺）作为新的D-？受体和/或相关的四烷基二萘嵌苯作为新的D-？-一个供体，将被准备和评估为电流的潜在整流器。这些基团的分子轨道水平很好地位于D-？-一项任务。基于二萘嵌苯的供体和受体具有两个合成柄，允许方便地连接-？-他们之间的桥梁，以及“尾巴”的另一端。需要这些尾部来提高溶解度，并允许形成评价精馏所需的单层。将控制单层膜在D-？- A还是A-？通过适当选择尾部来实现三维定向。相对极性的聚乙二醇（PEG）的尾巴提出了一些目标应改善电流相比，非极性烷基尾巴。鉴于最近D-？- A多层以及从D-？- A单层，Aviram-Ratner模型适当适用于D-？- A单层。拟议的研究将测试这些系统。. D-？- A靶将在密西西比大学合成，并将在亚拉巴马大学评估成膜和电性能。分子尺度整流的研究具有深远的实际意义，因为它可以使电子器件大大小型化。这是纳米电子学领域的一个重要目标。该项目为在培训来自密西西比和亚拉巴马的年轻少数民族科学家方面取得实质性进展提供了一个重要机会。

The Aviram-Ratner model of orbital energy levels predicts that monolayer arrays of Donor Sigma-Acceptor (D-?-A) molecules will pass electrons in only one direction, that is, D-?-A molecules should be able to rectify electricity. In this project a new class of materilas incorporating perylenebis(dicarboximide) as a new D-?-A acceptor, and/or a related tetralkylperylene as a new D-?-A donor, will be prepared and evaluated as potential rectifiers of electrical current. The molecular orbital levels of these groups are well situated for the D-?-A task. The perylene-based donors and acceptors have two synthetic handles, allowing the convenient attachment of the -?- bridge between them, as well as "tails" to the other ends. These tails are required both to improve solubility and to permit the formation of the monolayers required to evaluate rectification. Monolayer films will be controlled to form in either the D-?-A or A-?-D orientation by the appropriate selection of tails. The relatively polar polyethyleneglycol (PEG) tails proposed for some targets should improve current flow compared to nonpolar alkyl tails. Whereas rectification has been reported recently from D-?-A multilayers as well as from D-?-A monolayers, the Aviram-Ratner model properly applies to D-?-A monolayers. The proposed research will test these systems. . The D-?-A targets will be synthesized at the University of Mississippi, and will be evaluated for film-formation and electrical properties at the University of Alabama.%%%The investigation of molecular-scale rectification is of far-reaching practical interest because it could lead to greatly miniaturized electronic devices. This is an important goal in the world of nanoelectronics. This project provides a significant opportunity for substantial advancements in the training of young minority scientists from Mississippi and Alabama.