Design, synthesis and development of shapeshifting organic molecules
A hallmark of biological systems is their ability to respond to changes in their environment and to perform specific tasks by structural changes. Despite a great deal of interests in this, chemists are only now beginning to design and utilize synthetic molecules to perform specific tasks by changes in their shape or structure. As part of our interest in this area, we have designed and prepared shapeshifting organic molecules. These unique structures, which are build around the core of an organic molecules known as bullvalene, has the remarkable ability to spontaneously interconvert between dozens, hundreds, or even thousands of discrete structures by intramolecular rearrangements. We have now prepared the core structure on gram scale and have developed protocols to introduce various groups and probes into the side arms.
We have also demonstrated that a 13C labeled bullvalene core can act as a reporter for binding events and generate unique signals for even closely related analytes such as C60 and C70. In this context, shapeshifting organic molecules have the potential to function as non-invasive sensors for applications in biomedical imaging and surface science.
Selected publications:
(40) Lippert, A. R.; Naganawa, A.; Keleshian, V. L.; Bode, J. W. external page"Synthesis of Phototrappable Shape-Shifting Molecules for Adaptive Guest Binding" J. Am. Chem. Soc. 2010, 132, 15790–15799.
(50) He, M.; Bode, J. W. external page"Racemization as a stereochemical measure of dynamics and robustness in shape-shifting organic molecules" Proc. Nat. Acad. Sci. U.S.A. 2011, 36, 14752–14756.
(63) Larson, K. K.; He, M.; Teichert, J. F.; Naganawa, A.; Bode, J. W. external page"Chemical Sensing with Shapeshifting Organic Molecules" Chem. Sci. 2012, 3, 1825–1828.
(79) He, M.; Bode, J. W. external page"E pluribus unum: Isolation, structure determination, network analysis and DFT studies of a single metastable structure from a shapeshifting mixture of 852 bullvalene structural isomers" Org. Biomol. Chem. 2013, 11, 1306–1317.
(82) Teichert, J. F.; Mazunin, D.; Bode, J. W. external page"Chemical Sensing of Polyols with Shapeshifting Boronic Acids as a Self-Contained Sensor Array"J. Am. Chem. Soc. 2013, 135, 11314–11321.