Mitglied der HelmholtzGemeinschaft SINE 2020 Chemical Deuteration WP

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Mitglied der Helmholtz-Gemeinschaft SINE 2020 – Chemical Deuteration WP FZJ Contributions Jürgen Allgaier Jülich

Mitglied der Helmholtz-Gemeinschaft SINE 2020 – Chemical Deuteration WP FZJ Contributions Jürgen Allgaier Jülich Centre for Neutron Science JCNS and Institute for Complex Systems ICS Forschungszentrum Jülich Gmb. H

Tasks Ø Novel route for isoprene synthesis (D 5. 3, month 15) Ø Synthesis

Tasks Ø Novel route for isoprene synthesis (D 5. 3, month 15) Ø Synthesis of deuterium labelled polythiophene based block copolymers (D 5. 5, month 20) Ø Synthesis of deuterium labelled polylactic acid (D 5. 8, month 30) (Synthesis of L- and D-lactic acid, ESS deliverable D 5. 4) Ø (PEG/PEGylated lipids, D 5. 11) 10 November 2020 Folie 2

Novel route for isoprene synthesis Ø accessibility/costs of starting compounds Ø monomer purity Ø

Novel route for isoprene synthesis Ø accessibility/costs of starting compounds Ø monomer purity Ø deuteration degree 10 November 2020 Folie 3

Synthesis of deuterium labelled polythiophene based block copolymers 1. GRIM Polymerization of P 3

Synthesis of deuterium labelled polythiophene based block copolymers 1. GRIM Polymerization of P 3 HT 10 November 2020 Folie 4

Synthesis of deuterium labelled polythiophene based block copolymers 2. Diblocks Ø P 3 HT:

Synthesis of deuterium labelled polythiophene based block copolymers 2. Diblocks Ø P 3 HT: structural quality, chemical functionalization Ø impurities: homopolymers, salts Ø deuteration scenarios 10 November 2020 Folie 5

Synthesis of deuterium labelled polylactic acid • lactic acid (h and d): ESS •

Synthesis of deuterium labelled polylactic acid • lactic acid (h and d): ESS • lactide: FZJ • poly(lactic acid): RWTH (Prof. Okuda) 10 November 2020 Folie 6

Synthesis of deuterium labelled polylactic acid Lactide synthesis • D-lactic acid (h), 10 g

Synthesis of deuterium labelled polylactic acid Lactide synthesis • D-lactic acid (h), 10 g - LA 52% LA, 48% open dimer 28% water open dimer, 1 H 10 November 2020 Folie 7

Synthesis of deuterium labelled polylactic acid • Conversion to lactide • Purification by sublimation,

Synthesis of deuterium labelled polylactic acid • Conversion to lactide • Purification by sublimation, recrystallization: (yield: 2 g, 35%) lactide open dimer, 1 H LA 10 November 2020 Folie 8

Synthesis of deuterium labelled polylactic acid • Polymerization (Dr. Beckerle, RWTH) [Zn. Et 2]/[Bn.

Synthesis of deuterium labelled polylactic acid • Polymerization (Dr. Beckerle, RWTH) [Zn. Et 2]/[Bn. OH]/[L-Lactide] 1 / 2 / 100 THF; 18 h; ambient temperature 96 % conversion (NMR) 13 C{1 H}NMR Mn D GPC (RI) 10 800 1. 15 Corrected 6 300 - Calculated 6 900 - iii iis/ isi sii 10 November 2020 Folie 9

PEG 1. Polymerization of EO (h and d) 2. End group functionalization 10 November

PEG 1. Polymerization of EO (h and d) 2. End group functionalization 10 November 2020 Folie 10

PEG Synthesis of maleimide functionalized PEGs 10 November 2020 Folie 11

PEG Synthesis of maleimide functionalized PEGs 10 November 2020 Folie 11