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Comparison of “Polynaphthalenes” Prepared by Two Mechanistically Distinct Routes

M1 Colloquium in Division Frontier Materials Science in 2005. Comparison of “Polynaphthalenes” Prepared by Two Mechanistically Distinct Routes. Tobe Laboratory Hiroyuki Kuge. Contents. Introuction. Experiments. IR spectroscopy TGA MALDI-TOF MS & LDI-TOF MS 13 C CPMAS NMR spectroscopy.

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Comparison of “Polynaphthalenes” Prepared by Two Mechanistically Distinct Routes

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  1. M1 Colloquium in Division Frontier Materials Science in 2005 Comparison of “Polynaphthalenes” Prepared by Two Mechanistically Distinct Routes Tobe Laboratory Hiroyuki Kuge

  2. Contents Introuction Experiments IR spectroscopy TGA MALDI-TOF MS & LDI-TOF MS 13C CPMAS NMR spectroscopy Summary

  3. Cyclization of Enediyne cis-1,5-hexadiyne-3-ene benzene 1,4-benzenediradical Bergman cyclization

  4. Polymerization of Two Routes Polymerization by Kumada Coupling Polymerization by Bergman cyclization

  5. IR spectroscopy IR (KBr): 3062 (w), 3037 (m), 1506 (m), 1370 (m), 953 (m), 837 (m), 758 (s) cm-1. IR (KBr): 3298 (w), 3060 (m), 3024 (m), 2104 (vw), 1596 (m), 1476 (m), 874 (w), 754 (s) cm-1. rf. IR(KBr): 3054 (w), 3042 (w), 1506 (w), 1376 (m), 948 (w), 848 (w), 802 (s) 778 (s) 760 (s) cm-1. α IR:赤外分光法

  6. TGA Poly(1,4-dibromonaphthalene) Poly(o-diethynylbenzene) TGA:熱重量分析

  7. Pyrolysis GC-MS of poly(1,4-dibromonaphthalene) naphthalene 80% methylnaphthalene 8.4% dimethylnaphthalene 1.6%

  8. Pyrolysis GC-MS of a-ternaphthyl a naphthalene 91% methylnaphthalene 4.4%

  9. Pyrolysis GC-MS of poly(o-diethynylbenzene) naphthalene 24% methylnaphthalene 20% methylindene 24% dimethylnaphthalene 6.5% indene 22%

  10. MALDI-TOF MS

  11. MALDI-TOF MS of poly(1,4-dibromonaphthalene) MALDI:マトリックス支援レーザー脱離イオン化法

  12. MALDI-TOF MS of of a-ternaphthyl a

  13. LDI-TOF MS of poly(o-diethynylbenzene) LDI:レーザー脱離イオン化法

  14. CPMAS 13C NMR of poly(1,4-dibromonaphthalene) a

  15. CPMAS 13C NMR of poly(o-diethynylbenzene) a

  16. Suggest Mechanism of Radical Species F attack B C E D

  17. Intermolecular Addition of Radical D D + monomer

  18. Summary The polymers prepared by two routes are structurally distinct. Spectroscopic and spectrometric data indicate that the poly(1,4-dibromonaphthalene) is a poly(1,4-naphthalene), whereas the poly(o-diethynylbenzene) contains five-membered rings. In light of these dissimilarities, this roport suggests that these latter polymers not be represented as a poly(1,4-naphthalene).

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