Design, Synthesis and Supramolecular Assembly of Furan-Based Macrocycles: Understanding Intra- and Intermolecular Conjugation

呋喃基大环化合物的设计、合成和超分子组装:了解分子内和分子间共轭

基本信息

  • 批准号:
    2109065
  • 负责人:
  • 金额:
    $ 44.82万
  • 依托单位:
  • 依托单位国家:
    美国
  • 项目类别:
    Standard Grant
  • 财政年份:
    2021
  • 资助国家:
    美国
  • 起止时间:
    2021-07-01 至 2024-06-30
  • 项目状态:
    已结题

项目摘要

With the support of the Macromolecular, Supramolecular and Nanochemistry Program in the NSF Division of Chemistry, Drs. Kevin Noonan and Tomasz Kowalewski of Carnegie Mellon University aim to develop and explore a new class of cyclic (or ring-like) organic molecules comprised of smaller rings (“rings of rings”). Generally, the path to making cyclic molecules involves bending linear molecules to join the ends together. As the size of the ring increases, it can be difficult to make the “ends meet” resulting in lower yield of the desired structure. Noonan and Kowalewski recently discovered that short linear chains of small furan rings can be modified in such a way that they spontaneously bend into macrocyclic ring-like shapes. They will be exploring the extension of this method to different variants of small rings to tune the properties for different potential applications. In these cyclic structures, a portion of the electrons reside in so-called pi-bonds, which under certain conditions enables them to flow freely such that the material behaves as a metal or semiconductor rather than an insulator. As such, they belong to the family of “green” organic electronic materials that can be derived from biomass, with high promise for sustainable energy applications such as solar cells, displays, and catalysts for generation of fuels and chemicals. The interdisciplinary character of this work will lead to training of chemists with a unique skill set encompassing chemical synthesis, novel methods, and advanced computational tools facilitating precise, efficient, and environmentally friendly chemical synthesis. The PIs will also use social media and podcasts to raise public awareness on key scientific concepts of essential societal importance such as energy, sustainability, and health.Drs. Noonan and Kowalewski and their research teams will use a combination of synthesis, computation, and characterization to build a library of furan macrocycles and map the interplay between their structure and properties. The key synthetic strategy will involve using structure-directing ester side groups to promote efficient cyclization and extend it to achieve precise control of supramolecular assembly of these molecules. Computation will play a particularly important role in the studies of self-assembly by allowing exploration of a wide range of candidate structures and scenarios. It will help in determining the nature of intra- and intermolecular organization of the resulting nanostructures. Mapping the molecular and supramolecular properties of these materials will be paralleled, and correlated, with the investigation of their behavior in redox, charge transport and ion-binding processes. In addition, work on conjugated macrocycles will advance fundamental understanding of aromaticity by addressing key questions about the impact of molecular structure and conjugation on aromatic stabilization energy.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.
在NSF化学部大分子,超分子和纳米化学计划的支持下,卡内基梅隆大学的Kevin Noonan和Tomasz Kowalewski博士旨在开发和探索一类由较小环组成的新型环状(或环状)有机分子(“环的环”)。通常,制造环状分子的途径包括弯曲线性分子以将末端连接在一起。随着环的尺寸增加,可能难以使“端部相接”,导致所需结构的产率较低。努南和科瓦莱夫斯基最近发现,小呋喃环的短线性链可以以这样一种方式修饰,即它们自发地弯曲成大环环状形状。他们将探索将这种方法扩展到小环的不同变体,以调整不同潜在应用的属性。在这些环状结构中,一部分电子驻留在所谓的π键中,这在某些条件下使它们能够自由流动,使得材料表现为金属或半导体而不是绝缘体。因此,它们属于可衍生自生物质的“绿色”有机电子材料家族,对于可持续能源应用具有很高的前景,例如太阳能电池、显示器以及用于产生燃料和化学品的催化剂。这项工作的跨学科性质将导致培养具有独特技能的化学家,包括化学合成,新方法和先进的计算工具,促进精确,高效和环保的化学合成。研究所还将利用社交媒体和播客提高公众对能源、可持续发展和健康等具有重要社会意义的关键科学概念的认识。努南博士和科瓦莱夫斯基博士及其研究团队将利用合成、计算和表征相结合的方法建立呋喃大环化合物库,并绘制其结构和性质之间的相互作用。关键的合成策略将涉及使用结构导向酯侧基来促进有效的环化,并将其扩展以实现对这些分子的超分子组装的精确控制。计算将在自组装的研究中发挥特别重要的作用,允许探索广泛的候选结构和场景。这将有助于确定所得纳米结构的分子内和分子间组织的性质。这些材料的分子和超分子性质的映射将与它们在氧化还原、电荷传输和离子结合过程中的行为的调查相关联。此外,共轭大环的研究将通过解决分子结构和共轭对芳香稳定能的影响等关键问题,推进对芳香性的基本理解。该奖项反映了NSF的法定使命,并通过使用基金会的知识价值和更广泛的影响审查标准进行评估,被认为值得支持。

项目成果

期刊论文数量(3)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
Design, Synthesis and Aromaticity of an Alternating Cyclo[4]Thiophene[4]Furan
  • DOI:
    10.1002/chem.202300477
  • 发表时间:
    2023-05-16
  • 期刊:
  • 影响因子:
    4.3
  • 作者:
    Kawakami,Manami;Sharma,Dhruv;Noonan,Kevin J. T.
  • 通讯作者:
    Noonan,Kevin J. T.
Cholesterol side groups in Helical Poly(3-alkylesterfurans)
螺旋聚(3-烷基酯呋喃)中的胆固醇侧基
  • DOI:
    10.1038/s41428-022-00741-w
  • 发表时间:
    2023
  • 期刊:
  • 影响因子:
    2.8
  • 作者:
    Kawakami, Manami;Downey, Payton;Peteanu, Linda;Bernhard, Stefan;Noonan, Kevin J.
  • 通讯作者:
    Noonan, Kevin J.
Statistical copolymers of thiophene-3-carboxylates and selenophene-3-carboxylates; 77 Se NMR as a tool to examine copolymer sequence in selenophene-based conjugated polymers
噻吩-3-羧酸酯和硒吩-3-羧酸酯的统计共聚物;
  • DOI:
    10.1039/d2py00777k
  • 发表时间:
    2022
  • 期刊:
  • 影响因子:
    4.6
  • 作者:
    Kawakami, Manami;Schulz, Karl H.;Varni, Anthony J.;Tormena, Claudio F.;Gil, Roberto R.;Noonan, Kevin J.
  • 通讯作者:
    Noonan, Kevin J.
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Kevin Noonan其他文献

Examining Technical Aspects of the Monoclonal Antibody Immobilisation of Granulocyte Antigen Assay
检查粒细胞抗原测定的单克隆抗体固定化的技术方面
  • DOI:
  • 发表时间:
    1997
  • 期刊:
  • 影响因子:
    2.7
  • 作者:
    R. Minchinton;Kevin Noonan;T. J. Johnson
  • 通讯作者:
    T. J. Johnson

Kevin Noonan的其他文献

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{{ truncateString('Kevin Noonan', 18)}}的其他基金

Design and Synthesis of Robust Cationic Polymers for Stable and Efficient Anion-Exchange Membranes
用于稳定高效阴离子交换膜的鲁棒阳离子聚合物的设计与合成
  • 批准号:
    1809658
  • 财政年份:
    2018
  • 资助金额:
    $ 44.82万
  • 项目类别:
    Standard Grant
CAREER: Controlled Polycondensation Techniques as a Route to Novel Semiconducting Polymer Architectures
职业:受控缩聚技术作为新型半导体聚合物架构的途径
  • 批准号:
    1455136
  • 财政年份:
    2015
  • 资助金额:
    $ 44.82万
  • 项目类别:
    Continuing Grant

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新型滤波器综合技术-直接综合技术(Direct synthesis Technique)的研究及应用
  • 批准号:
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  • 批准号:
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