Stereoselective ROP of rac- and meso-lactides using achiral TBD as catalyst

Sebastien Moins; Sebastien Hoyas; Vincent Lemaur; Beste  Orhan; Kayla Delle Chiaie; Roberto Lazzaroni; Daniel Taton; Andrew Dove; Olivier Coulembier

doi:10.3390/catal10060620

Stereoselective ROP of rac- and meso-lactides using achiral TBD as catalyst

Sebastien Moins, Sebastien Hoyas, Vincent Lemaur, Beste Orhan, Kayla Delle Chiaie, Roberto Lazzaroni, Daniel Taton, Andrew Dove, Olivier Coulembier

Chemistry

Research output: Contribution to journal › Article › peer-review

6 Citations (Scopus)

132 Downloads (Pure)

Abstract

1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) polymerizes rac-lactide (rac-LA) to form highly isotactic polylactide (PLA) with a P_m = 0.88, while meso-LA yields heterotactic PLA (P_m ~ 0.8) at −75 °C. The stereocontrol of the cryogenic-based ring-opening polymerization comes from a perfect imbrication of both chiral LA and the propagating chiral end-group interacting with the achiral TBD catalyst.

Original language	English
Article number	620
Number of pages	8
Journal	Catalysts
Volume	10
Issue number	6
DOIs	https://doi.org/10.3390/catal10060620
Publication status	Published - 3 Jun 2020

Keywords

TBD
lactide
organocatalyst
ring-opening polymerization
stereocontrol

Access to Document

10.3390/catal10060620Licence: Creative Commons: Attribution (CC BY)

Moins_et_al_Stereoselective_ROP_of_rac_and_meso_lactides_using_achiral_TBD_as_catalyst_Catalysts_2020Final published version, 1.47 MBLicence: Creative Commons: Attribution (CC BY)

https://doi.org/10.3390/catal10060620Licence: Creative Commons: Attribution (CC BY)

Cite this

@article{2ba5af1fc7764a12811d1fd2128f4bfa,

title = "Stereoselective ROP of rac- and meso-lactides using achiral TBD as catalyst",

abstract = "1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) polymerizes rac-lactide (rac-LA) to form highly isotactic polylactide (PLA) with a Pm = 0.88, while meso-LA yields heterotactic PLA (Pm ~ 0.8) at −75 °C. The stereocontrol of the cryogenic-based ring-opening polymerization comes from a perfect imbrication of both chiral LA and the propagating chiral end-group interacting with the achiral TBD catalyst.",

keywords = "TBD, lactide, organocatalyst, ring-opening polymerization, stereocontrol",

author = "Sebastien Moins and Sebastien Hoyas and Vincent Lemaur and Beste Orhan and {Delle Chiaie}, Kayla and Roberto Lazzaroni and Daniel Taton and Andrew Dove and Olivier Coulembier",

year = "2020",

month = jun,

day = "3",

doi = "10.3390/catal10060620",

language = "English",

volume = "10",

journal = "Catalysts",

issn = "2073-4344",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "6",

}

TY - JOUR

T1 - Stereoselective ROP of rac- and meso-lactides using achiral TBD as catalyst

AU - Moins, Sebastien

AU - Hoyas, Sebastien

AU - Lemaur, Vincent

AU - Orhan, Beste

AU - Delle Chiaie, Kayla

AU - Lazzaroni, Roberto

AU - Taton, Daniel

AU - Dove, Andrew

AU - Coulembier, Olivier

PY - 2020/6/3

Y1 - 2020/6/3

N2 - 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) polymerizes rac-lactide (rac-LA) to form highly isotactic polylactide (PLA) with a Pm = 0.88, while meso-LA yields heterotactic PLA (Pm ~ 0.8) at −75 °C. The stereocontrol of the cryogenic-based ring-opening polymerization comes from a perfect imbrication of both chiral LA and the propagating chiral end-group interacting with the achiral TBD catalyst.

AB - 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) polymerizes rac-lactide (rac-LA) to form highly isotactic polylactide (PLA) with a Pm = 0.88, while meso-LA yields heterotactic PLA (Pm ~ 0.8) at −75 °C. The stereocontrol of the cryogenic-based ring-opening polymerization comes from a perfect imbrication of both chiral LA and the propagating chiral end-group interacting with the achiral TBD catalyst.

KW - TBD

KW - lactide

KW - organocatalyst

KW - ring-opening polymerization

KW - stereocontrol

UR - http://www.scopus.com/inward/record.url?scp=85086050274&partnerID=8YFLogxK

U2 - 10.3390/catal10060620

DO - 10.3390/catal10060620

M3 - Article

SN - 2073-4344

VL - 10

JO - Catalysts

JF - Catalysts

IS - 6

M1 - 620

ER -

Stereoselective ROP of rac- and meso-lactides using achiral TBD as catalyst

Abstract

Keywords

Access to Document

Fingerprint

Cite this