Precision synthesis of fluorene-thiophene alternating copolymer by means of Suzuki-Miyaura catalyst-transfer condensation polymerization: importance of the position of alkyl substituent on thiophene of biaryl monomer to suppress disproportionation

2021 ◽  
Author(s):  
Yu Tokita ◽  
Masaru Katoh ◽  
Kentaro Kosaka ◽  
Yoshihiro Ohta ◽  
Tsutomu Yokozawa
Keyword(s):  
Alkyl Substituent ◽  
Condensation Polymerization ◽  
Arylboronic Acid ◽  
Alternating Copolymer ◽  
Precision Synthesis ◽  
Acid Esters ◽  
Model Reactions

Suzuki-Miyaura catalyst-transfer condensation polymerization (CTCP) of fluorene-thiophene biaryl monomers was investigated for the synthesis of well-defined poly(fluorene-alt-thiophene). Model reactions of α,ω-dibromo(fluorene-thiophene) with arylboronic acid esters showed that t-Bu3P Pd and...

Precision Synthesis of n-Type π-Conjugated Polymers in Catalyst-Transfer Condensation Polymerization

2012 ◽  
Vol 1 (7) ◽  
pp. 862-866 ◽  
Author(s):  
Tsutomu Yokozawa ◽  
Yutaka Nanashima ◽  
Yoshihiro Ohta
Keyword(s):  
Conjugated Polymers ◽  
Condensation Polymerization ◽  
Precision Synthesis

scholarly journals Modified Conditions for Copper-catalyzed ipso-Thiolation of Arylboronic Acid Esters with Thiosulfonates

2018 ◽  
Vol 47 (1) ◽  
pp. 85-88 ◽  
Author(s):  
Kazuya Kanemoto ◽  
Suguru Yoshida ◽  
Takamitsu Hosoya
Keyword(s):  
Arylboronic Acid ◽  
Acid Esters

Synthesis of donor-acceptor alternating copolymer by uncatalyzed condensation polymerization

2013 ◽  
Vol 21 (5) ◽  
pp. 463-465 ◽  
Author(s):  
Seung-Jin Yoo ◽  
Chan Woo Jeon ◽  
Jong-Jin Ha ◽  
Sang Young Nam ◽  
Sung Chul Shin ◽  
...  
Keyword(s):  
Condensation Polymerization ◽  
Alternating Copolymer ◽  
Donor Acceptor

Catalyst-transfer condensation polymerization for precision synthesis of π-conjugated polymers

2012 ◽  
Vol 85 (3) ◽  
pp. 573-587 ◽  
Author(s):  
Tsutomu Yokozawa ◽  
Yutaka Nanashima ◽  
Haruhiko Kohno ◽  
Ryosuke Suzuki ◽  
Masataka Nojima ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Conjugated Polymers ◽  
Ni Catalyst ◽  
Condensation Polymerization ◽  
End Groups ◽  
Precision Synthesis ◽  
Polymerization Method ◽  
Low Solubility ◽  
End Group ◽  
Coupling Polymerization

Catalyst-transfer condensation polymerization, in which the catalyst activates the polymer end-group, followed by reaction with the monomer and transfer of the catalyst to the elongated polymer end-group, has made it feasible to control the molecular weight, polydispersity, and end-groups of π-conjugated polymers. In this paper, our recent progress of Kumada–Tamao Ni catalyst-transfer coupling polymerization and Suzuki–Miyaura Pd catalyst-transfer coupling polymerization is described. In the former polymerization method, the polymerization of Grignard pyridine monomers was investigated for the synthesis of well-defined n-type π-conjugated polymers. Para-type pyridine monomer, 3-alkoxy-2-bromo-5-chloromagnesiopyridine, afforded poly(pyridine-2,5-diyl) with low solubility in the reaction solvent, whereas meta-type pyridine monomer, 2-alkoxy-5-bromo-3-chloromagnesio-pyridine, yielded soluble poly(pyridine-3,5-diyl) with controlled molecular weight and low polydispersity. In Suzuki–Miyaura catalyst-transfer coupling polymerization, t-Bu3PPd(Ph)Br was an effective catalyst, and well-defined poly(p-phenylene) and poly(3-hexylthiophene) (P3HT) were obtained by concomitant use of CsF/18-crown-6 as a base in tetrahydrofuran (THF) and a small amount of water.

Occurrence and Origin of the Tropylium Ion in the Mass Spectra of Arylboronic Acid Esters

1971 ◽  
Vol 49 (10) ◽  
pp. 1766-1770 ◽  
Author(s):  
R. J. Bose ◽  
M. D. Peters
Keyword(s):  
Mass Spectra ◽  
Phenylboronic Acid ◽  
Arylboronic Acid ◽  
Acid Esters

The mass spectra of a number of phenylboronic acid esters of 1,2- and 1,3-diols are examined and the presence and origin of the tropylium rearrangement ion is established.

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