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LEAPS-MPS: Development of New Photoacid Catalyzed Reactions for Organic Synthesis

LEAPS-MPS：新型光酸催化有机合成反应的开发

基本信息

批准号：
2137600
负责人：
Joseph Badillo
金额：
$ 21.98万
依托单位：
Seton Hall University
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：
2021-09-15 至 2023-08-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=2137600&HistoricalAwards=false
关键词：
LEAPS MPS Development New Photoacid

项目摘要

This award is funded in whole or in part under the American Rescue Plan Act of 2021 (Public Law 117-2). In this project, funded by the Mathematical and Physical Sciences Directorate and housed in the Chemistry Division, Professor Joseph Badillo and his students at Seton Hall University will study photoacids and photoacid catalysis to help design new chemical reactions that will be important in synthesizing new organic (carbon-based) molecules. A photoacid is a weak acid in its normal state, and only upon irradiation with light does it become a strong acid, and thus catalytically active (able to speed up reactions). This dependence on light-activation offers temporal- and spatial-control not possible with traditional acid catalysis. Despite the unique possibilities of photoacid catalysis, the synthesis and characterization of new photoacids and the development of new photoacid catalyzed reactions remains relatively unexplored. Prof. Badillo also proposes a broadening participation plan that includes having his students present their research at URM-serving conferences such as NOBCChE, working with ACS Project SEED to provide research experiences for URM high school students, and working with several Seton Hall University student organizations to bring science outreach to local minority-serving high schools.Professor Badillo will perform experiments leading to improved understanding of common photoacid catalysts’ photophysical properties by measuring excited state lifetimes (t) and acidities (pKa*). A series of non-photoracemizable chiral photoacids will be designed, synthesized and characterized, and the use of photoacid catalysis will be explored in the context of C–X (X = H, O, C) bond-forming reactions, including asymmetric excited-state proton transfer, glycosylation, and acetalization reactions. The use of photoacid generators such as halonium and sulfonium ions in the context of catalysis will also be investigated. Prof. Badillo’s plan for integrating research and broadening participation-oriented outreach activities will both bring underrepresented minority high school students to Seton Hall University for research experiences, and send Seton Hall students into local schools for science outreach activities.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.

该奖项全部或部分根据2021年美国救援计划法案（公法117-2）资助。在这个项目中，由数学和物理科学理事会资助，并设在化学部，教授约瑟夫巴迪略和他的学生在西顿霍尔大学将研究光酸和光酸催化，以帮助设计新的化学反应，这将是重要的合成新的有机（碳基）分子。光酸在正常状态下是一种弱酸，只有在光照射下才会变成强酸，从而具有催化活性（能够加速反应）。这种对光活化的依赖提供了传统酸催化不可能实现的时间和空间控制。尽管光酸催化具有独特的可能性，但新的光酸的合成和表征以及新的光酸催化反应的开发仍然相对未被探索。 Badillo还提出了一个扩大参与计划，包括让他的学生在URM服务会议上展示他们的研究，如NOBCChE，与ACS项目SEED合作，为URM高中学生提供研究经验，并与几个西顿霍尔大学的学生组织合作，将科学推广到当地少数民族-Badillo教授将通过测量激发态寿命（t）和酸度（pKa*）来进行实验，从而提高对常见光酸催化剂物理特性的理解。设计、合成和表征了一系列不可光酰化的手性光酸，并将探索光酸催化在C-X（X = H，O，C）键形成反应中的应用，包括不对称激发态质子转移、糖基化和缩醛化反应。还将研究在催化作用中使用光生酸剂如卤离子和锍离子。 Badillo教授的整合研究和扩大以参与为导向的外展活动的计划，既将使代表性不足的少数民族高中学生到西顿霍尔大学进行研究经验，也将西顿霍尔学生送到当地学校进行科学外展活动。这个奖项反映了NSF的法定使命，并通过使用基金会的智力价值和更广泛的影响审查标准进行评估，被认为值得支持。