Mechanically Triggered Carbon Monoxide Release with Turn-On Aggregation-Induced Emission

被引:78
作者
Sun, Yunyan [1 ]
Neary, William J. [1 ,2 ]
Burke, Zachary P. [1 ]
Qian, Hai [2 ]
Zhu, Lingyang [1 ]
Moore, Jeffrey S. [1 ,2 ]
机构
[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA
[2] Univ Illinois, Beckman Inst Adv Sci & Technol, Urbana, IL 61801 USA
基金
美国国家科学基金会;
关键词
POLYMERS; MECHANOCHEMISTRY; ACTIVATION;
D O I
10.1021/jacs.1c12108
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Polymers that release functional small molecules under mechanical stress potentially serve as next-generation materials for catalysis, sensing, and mechanochemical dynamic therapy. To further expand the function of mechanoresponsive materials, the discovery of chemistries capable of small molecule release are highly desirable. In this report, we detail a nonscissile bifunctional mechanophore (i.e., dual mechano-activated properties) based on a unique mechanochemical reaction involving norborn-2-en-7-one (NEO). One property is the release of carbon monoxide (CO) upon pulsed solution ultrasonication. A release efficiency of 58% is observed at high molecular weights (M-n = 158.8 kDa), equating to similar to 154 molecules of CO released per chain. The second property is the bright cyan emission from the macromolecular product in its aggregated state, resulting in a turn-on fluorescence readout coincident with CO release. This report not only demonstrates a unique strategy for the release of small molecules in a nonscissile way but also guides future designs of force-responsive aggregation-induced emission (AIE) luminogens.
引用
收藏
页码:1125 / 1129
页数:5
相关论文
共 35 条
  • [1] Empowering mechanochemistry with multi-mechanophore polymer architectures
    Bowser, Brandon H.
    Craig, Stephen L.
    [J]. POLYMER CHEMISTRY, 2018, 9 (26) : 3583 - 3593
  • [2] The cascade unzipping of ladderane reveals dynamic effects in mechanochemistry
    Chen, Zhixing
    Zhu, Xiaolei
    Yang, Jinghui
    Mercer, Jaron A. M.
    Burns, Noah Z.
    Martinez, Todd J.
    Xia, Yan
    [J]. NATURE CHEMISTRY, 2020, 12 (03) : 302 - +
  • [3] Proton-Coupled Mechanochemical Transduction: A Mechanogenerated Add
    Diesendruck, Charles E.
    Steinberg, Brian D.
    Sugai, Naoto
    Silberstein, Meredith N.
    Sottos, Nancy R.
    White, Scott R.
    Braun, Paul V.
    Moore, Jeffrey S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) : 12446 - 12449
  • [4] Mechanochemical Activation of Covalent Bonds in Polymers with Full and Repeatable Macroscopic Shape Recovery
    Gossweiler, Gregory R.
    Hewage, Gihan B.
    Soriano, Gerardo
    Wang, Qiming
    Welshofer, Garrett W.
    Zhao, Xuanhe
    Craig, Stephen L.
    [J]. ACS MACRO LETTERS, 2014, 3 (03) : 216 - 219
  • [5] Aggregation-induced emission: phenomenon, mechanism and applications
    Hong, Yuning
    Lam, Jacky W. Y.
    Tang, Ben Zhong
    [J]. CHEMICAL COMMUNICATIONS, 2009, (29) : 4332 - 4353
  • [6] A Polymer with "Locked" Degradability: Superior Backbone Stability and Accessible Degradability Enabled by Mechanophore Installation
    Hsu, Tze-Gang
    Zhou, Junfeng
    Su, Hsin-Wei
    Schrage, Briana R.
    Ziegler, Christopher J.
    Wang, Junpeng
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (05) : 2100 - 2104
  • [7] Mechanically Triggered Release of Functionally Diverse Molecular Payloads from Masked 2-Furylcarbinol Derivatives
    Hu, Xiaoran
    Zeng, Tian
    Husic, Corey C.
    Robb, Maxwell J.
    [J]. ACS CENTRAL SCIENCE, 2021, 7 (07) : 1216 - 1224
  • [8] Mechanically Triggered Small Molecule Release from a Masked Furfuryl Carbonate
    Hu, Xiaoran
    Zeng, Tian
    Husic, Corey C.
    Robb, Maxwell J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (38) : 15018 - 15023
  • [9] Mechanochemical bond scission for the activation of drugs
    Huo, Shuaidong
    Zhao, Pengkun
    Shi, Zhiyuan
    Zou, Miancheng
    Yang, Xintong
    Warszawik, Eliza
    Loznik, Mark
    Goestl, Robert
    Herrmann, Andreas
    [J]. NATURE CHEMISTRY, 2021, 13 (02) : 131 - 139
  • [10] An esterase-activated click and release approach to metal-free CO-prodrugs
    Ji, Xingyue
    Ji, Kaili
    Chittavong, Vayou
    Yu, Bingchen
    Pan, Zhixiang
    Wang, Binghe
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (59) : 8296 - 8299