DOI: 10.1002/marc.200600286. Polyacetylene and Polynorbornene Derivatives Carrying TEMPO. Synthesis and Properties as Organic Radical Battery Materials

Polyacetylene and Polynorbornene Derivatives Carrying TEMPO. Synthesis and Properties as Organic Radical Battery Materials

10.1002/marc.200600286

Crossref journal-article

Wiley

Macromolecular Rapid Communications (311)

Abstract

AbstractSummary: 2,2,6,6‐Tetramethylpiperidine 1‐oxyl (TEMPO)‐containing N‐propargylamide HCCCH2NHCO‐4‐TEMPO (1), propargyl ester HCCCH2OCO‐4‐TEMPO (2), phenylacetylene derivative HCCC6H3‐3,4‐(CO2‐4‐TEMPO)2 (3), and norbornene diester monomers, NB‐2,3‐exo,exo‐(CH2OCO‐4‐TEMPO)2 (4), NB‐2,3‐endo,exo‐(COO‐4‐TEMPO)2 (5a), NB‐2,3‐endo,endo‐(COO‐4‐TEMPO)2 (5b) (NB = norbornene, TEMPO = 2,2,6,6‐tetramethyl‐1‐piperidinyloxyl) were synthesized and polymerized with rhodium and ruthenium catalysts. Monomers 2, 5a, and 5b gave polymers with number‐average molecular weights of 47 000–185 000 in 59–100% yields, while 1, 3, and 4 gave polymers insoluble in common organic solvents in 88–100% yields. The capacities of cells fabricated with poly(1), poly(2), and poly(3) were 67, 82, and 23 Ah · kg−1 based on the weight, respectively. The capacity of poly(5a)‐based cell reached the theoretical value (109 Ah · kg−1) of the polymer.Charge–discharge curves of poly(5a) at a current density of 0.13 mA · cm−2 (100 mA · g−1‐cathode active material) in the voltage range of 2.5–4.2 V.magnified imageCharge–discharge curves of poly(5a) at a current density of 0.13 mA · cm−2 (100 mA · g−1‐cathode active material) in the voltage range of 2.5–4.2 V.

Bibliography

Katsumata, T., Satoh, M., Wada, J., Shiotsuki, M., Sanda, F., & Masuda, T. (2006). Polyacetylene and Polynorbornene Derivatives Carrying TEMPO. Synthesis and Properties as Organic Radical Battery Materials. Macromolecular Rapid Communications, 27(15), 1206â1211. Portico.

Authors 6

Toru Katsumata (first)
Masaharu Satoh (additional)
Jun Wada (additional)
Masashi Shiotsuki (additional)
Fumio Sanda (additional)
Toshio Masuda (additional)

References 11 Referenced 97

10.1021/ja00995a061
10.1021/ma60057a038
10.1080/07366578208081062
10.1016/S0040-4039(03)00003-0
10.1021/ol051749n
10.1016/S0009-2614(02)00705-4
10.1016/j.electacta.2004.02.052
{'key': 'e_1_2_5_10_2', 'first-page': '2076', 'volume': '87', 'author': 'Satoh M.', 'year': '2004', 'journal-title': 'IEICE Trans. Electron.'} / IEICE Trans. Electron. by Satoh M. (2004)
10.1021/ic50092a027

Dates

Type	When
Created	19 years, 1 month ago (July 24, 2006, 9:46 a.m.)
Deposited	1 year, 10 months ago (Oct. 9, 2023, 9:34 p.m.)
Indexed	1 year, 1 month ago (July 28, 2024, 3:52 a.m.)
Issued	19 years, 1 month ago (July 24, 2006)
Published	19 years, 1 month ago (July 24, 2006)
Published Online	19 years, 1 month ago (July 24, 2006)
Published Print	19 years, 1 month ago (Aug. 2, 2006)

Funders 0

None

BibTeX

@article{Katsumata_2006, title={Polyacetylene and Polynorbornene Derivatives Carrying TEMPO. Synthesis and Properties as Organic Radical Battery Materials}, volume={27}, ISSN={1521-3927}, url={http://dx.doi.org/10.1002/marc.200600286}, DOI={10.1002/marc.200600286}, number={15}, journal={Macromolecular Rapid Communications}, publisher={Wiley}, author={Katsumata, Toru and Satoh, Masaharu and Wada, Jun and Shiotsuki, Masashi and Sanda, Fumio and Masuda, Toshio}, year={2006}, month=jul, pages={1206–1211} }

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  "abstract": "<jats:title>Abstract</jats:title><jats:p><jats:bold>Summary:</jats:bold> 2,2,6,6\u2010Tetramethylpiperidine 1\u2010oxyl (TEMPO)\u2010containing <jats:italic>N</jats:italic>\u2010propargylamide HC\uf8fdCCH<jats:sub>2</jats:sub>NHCO\u20104\u2010TEMPO (<jats:bold>1</jats:bold>), propargyl ester HC\uf8fdCCH<jats:sub>2</jats:sub>OCO\u20104\u2010TEMPO (<jats:bold>2</jats:bold>), phenylacetylene derivative HC\uf8fdCC<jats:sub>6</jats:sub>H<jats:sub>3</jats:sub>\u20103,4\u2010(CO<jats:sub>2</jats:sub>\u20104\u2010TEMPO)<jats:sub>2</jats:sub> (<jats:bold>3</jats:bold>), and norbornene diester monomers, NB\u20102,3\u2010<jats:italic>exo,exo</jats:italic>\u2010(CH<jats:sub>2</jats:sub>OCO\u20104\u2010TEMPO)<jats:sub>2</jats:sub> (<jats:bold>4</jats:bold>), NB\u20102,3\u2010<jats:italic>endo,exo</jats:italic>\u2010(COO\u20104\u2010TEMPO)<jats:sub>2</jats:sub> (<jats:bold>5a</jats:bold>), NB\u20102,3\u2010<jats:italic>endo,endo</jats:italic>\u2010(COO\u20104\u2010TEMPO)<jats:sub>2</jats:sub> (<jats:bold>5b</jats:bold>) (NB\u2009=\u2009norbornene, TEMPO\u2009=\u20092,2,6,6\u2010tetramethyl\u20101\u2010piperidinyloxyl) were synthesized and polymerized with rhodium and ruthenium catalysts. Monomers <jats:bold>2</jats:bold>, <jats:bold>5a</jats:bold>, and <jats:bold>5b</jats:bold> gave polymers with number\u2010average molecular weights of 47\u2009000\u2013185\u2009000 in 59\u2013100% yields, while <jats:bold>1</jats:bold>, <jats:bold>3</jats:bold>, and <jats:bold>4</jats:bold> gave polymers insoluble in common organic solvents in 88\u2013100% yields. The capacities of cells fabricated with poly(<jats:bold>1</jats:bold>), poly(<jats:bold>2</jats:bold>), and poly(<jats:bold>3</jats:bold>) were 67, 82, and 23 Ah\u2009\u00b7\u2009kg<jats:sup>\u22121</jats:sup> based on the weight, respectively. The capacity of poly(<jats:bold>5a</jats:bold>)\u2010based cell reached the theoretical value (109 Ah\u2009\u00b7\u2009kg<jats:sup>\u22121</jats:sup>) of the polymer.</jats:p><jats:p><jats:boxed-text content-type=\"graphic\" position=\"anchor\"><jats:caption><jats:p>Charge\u2013discharge curves of poly(<jats:bold>5a</jats:bold>) at a current density of 0.13 mA\u2009\u00b7\u2009cm<jats:sup>\u22122</jats:sup> (100 mA\u2009\u00b7\u2009g<jats:sup>\u22121</jats:sup><jats:sub>\u2010cathode active material</jats:sub>) in the voltage range of 2.5\u20134.2 V.</jats:p></jats:caption><jats:graphic xmlns:xlink=\"http://www.w3.org/1999/xlink\" mimetype=\"image/jpeg\" position=\"anchor\" specific-use=\"enlarged-web-image\" xlink:href=\"graphic/mgra001.jpg\"><jats:alt-text>magnified image</jats:alt-text><jats:caption><jats:p>Charge\u2013discharge curves of poly(<jats:bold>5a</jats:bold>) at a current density of 0.13 mA\u2009\u00b7\u2009cm<jats:sup>\u22122</jats:sup> (100 mA\u2009\u00b7\u2009g<jats:sup>\u22121</jats:sup><jats:sub>\u2010cathode active material</jats:sub>) in the voltage range of 2.5\u20134.2 V.</jats:p></jats:caption></jats:graphic></jats:boxed-text>\n</jats:p>",
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