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- Title
Preparation of Head-to-Tail Regioregular 6-(1-Alkenyl)-Functionalized Poly(pyridine-2,5-diyl) and its Post-Functionalization via Hydroboration.
- Authors
Grandl, Markus; Pammer, Frank
- Abstract
In this work, the preparation of head-to-tail regioregular poly(6-(1-tridecenyl)-pyridine-2,5-diyl) ( PPy) and its post-functionalization via hydroboration is described. PPy has been prepared via Kumada-coupling polycondensation with different catalytic systems. Number-average molecular weights of up to Mn = 14.7 kDa (PDI = 2.0, DPn = 60) can be obtained, as determined by gel permeation chromatography relative to polystyrene standards. PPy has been characterized by MALDI-TOF MS, optical spectroscopy, and cyclic voltammetry. The regioregularity of the material is confirmed by comparison with a head-to-head-tail-to-tail regioregular polybipyridine ( PBPy, Mn = 14.0 kDa, PDI = 1.5, DPn = 29). The 1-alkenyl-substituents in PPy have been introduced to provide functional groups for post-functionalization. Herein, it is also demonstrated that these internal double-bonds are sufficiently reactive to allow for hydroboration with 9 H-borabicyclo[3.3.1]nonane (9 H-BBN), to furnish an intermediate borylated polymer ( PPyHB). Treatment of PPyHB with strong acids, and characterization of the deborylated polymer PPyH2 proves quantitative conversion of the precursor polymer.
- Subjects
POLYPYRIDINES; PYRIDINE synthesis; DOUBLE bonds; SUBSTITUENTS (Chemistry); COUPLING reactions (Chemistry); HYDROBORATION; POLYCONDENSATION; CYCLIC voltammetry
- Publication
Macromolecular Chemistry & Physics, 2015, Vol 216, Issue 23, p2249
- ISSN
1022-1352
- Publication type
Article
- DOI
10.1002/macp.201500337