Tetrazine Polymers for Hydrogen Storage Douglas A. Loy, Departments of Materials Science and Engineering, & Chemistry and Biochemistry, University of Arizona, Tucson, AZ 85721-0012 Reversible hydrogenation of new, tetrazine based polymers will provide safe, non-cryogenic storage of hydrogen for fuel cells. Me
Me N N
N Me
N
N N N
N N
N
R'HN
Me
(1)
NHR'
* N N
N R'
R N R' n
polytetrazine
Our goals were to 1) prepare the first examples of tetrazine-based polymers from 3,6-bis(3,5-dimethyl-1Hpyrazol-1-yl)-s-tetrazine (1) reacting with diamines and dithiols and 2) investigate the hydrogenation/dehydrogenation chemistry of tetrazines. We have added the investigation of the Diels Alder cycloaddition chemistry of tetrazines and pyridazines. Me N
Me N N Me
N N
N N
Me Me +3H2
N
Me
HN N N
-3H2 Me
H N N H
N N NH
Me
Results: 1) Synthesis of tetrazine monomer (1) 2) New tetrazines from model reactions of (1) with amines 3) Demonstration of the reversibility of tetrazine hydrogenation 4) Preparation of the first tetrazine based polymers from diamines 5) Demonstration of tetrazine hydrogenation in solid polymers
