3-(2,2′:6′,2′′-Terpyridin-4′-yloxy)propyl toluene-4-sulfonate

Hoogenboom, Richard; Nakahashi, Akiko; Kickelbick, Guido; Chujo, Yoshiki; Schubert, Ulrich S.

doi:10.1107/s1600536807017229

Cited by 1 publication

(2 citation statements)

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“…Recrystallization of the prepared multi-tosylates from ethanol or ethanol–acetone mixtures directly gave single crystals suitable for X-ray analysis as we previously also observed for a tosylate adduct of 2,2’:6’,2’’ -terpyridine [ 20 ]. The obtained molecular structures and the packing diagrams for DiTos-A, DiTos-B, TetraTos and HexaTos are displayed in Figures 3–6, respectively.…”

Section: Resultsmentioning

confidence: 63%

“…1 . The advantages of multi-tosylate initiators are their straightforward syntheses starting from commercially available alcohols, their easy purification based on their high tendency to crystallize [ 19 – 20 ] and their stability under ambient conditions. In this contribution, we report the synthesis and crystal structures of various multi-tosylate initiators as well as their use for the initiation of the CROP of 2-ethyl-2-oxazoline for the formation of star-shaped poly(2-oxazoline)s.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and crystal structures of multifunctional tosylates as basis for star-shaped poly(2-ethyl-2-oxazoline)s

Hoogenboom¹,

Fijten²,

Kickelbick³

et al. 2010

Beilstein J. Org. Chem.

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SummaryThe synthesis of well-defined polymer architectures is of major importance for the development of complex functional materials. In this contribution, we discuss the synthesis of a range of multifunctional star-shaped tosylates as potential initiators for the living cationic ring-opening polymerization (CROP) of 2-oxazolines resulting in star-shaped polymers. The synthesis of the tosylates was performed by esterification of the corresponding alcohols with tosyl chloride. Recrystallization of these tosylate compounds afforded single crystals, and the X-ray crystal structures of di-, tetra- and hexa-tosylates are reported. The use of tetra- and hexa-tosylates, based on (di)pentaerythritol as initiators for the CROP of 2-ethyl-2-oxazoline, resulted in very slow initiation and ill-defined polymers, which is most likely caused by steric hindrance in these initiators. As a consequence, a porphyrin-cored tetra-tosylate initiator was prepared, which yielded a well-defined star-shaped poly(2-ethyl-2-oxazoline) by CROP as demonstrated by SEC with RI, UV and diode-array detectors, as well as by 1H NMR spectroscopy.

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Section: Resultsmentioning

confidence: 63%

Section: Introductionmentioning

confidence: 99%