Simple procedure for mono- and bis-end-functionalization of regioregular poly(3-hexylthiophene)s using chalcogens.

The efficient synthesis of regioregular poly(3-hexylthiophene-2,5-diyl)s (rr-P3HTs) capped with chalcogens using a simple quenching method is reported. Thiol (SH) end groups are selectively installed at the terminating end (ω-end) or at both the initiating (α-) and ω-ends using sulphur powder or triisopropylsilanethiol (TIPS-SH), respectively.

[1]  C. Luscombe,et al.  Room-temperature carbon–sulfur bond formation from Ni(II) σ-aryl complex via cleavage of the S–S bond of disulfide moieties , 2013 .

[2]  A. McNeil,et al.  Conjugated Polymer Synthesis via Catalyst-Transfer Polycondensation (CTP): Mechanism, Scope, and Applications , 2013 .

[3]  R. Verduzco,et al.  Amphiphilic poly(alkylthiophene) block copolymers prepared via externally initiated GRIM and click coupling , 2013 .

[4]  M. Stenzel.  Bioconjugation Using Thiols: Old Chemistry Rediscovered to Connect Polymers with Nature's Building Blocks. , 2013, ACS macro letters.

[5]  B. Sumpter,et al.  In Situ Formation of Pyridyl-Functionalized Poly(3-hexylthiophene)s via Quenching of the Grignard Metathesis Polymerization: Toward Ligands for Semiconductor Quantum Dots , 2012 .

[6]  K. Hashimoto,et al.  End-group stannylation of regioregular poly(3-hexylthiophene)s , 2012 .

[7]  R. Friend,et al.  Synthesis and photophysics of fully π-conjugated heterobis-functionalized polymeric molecular wires via Suzuki chain-growth polymerization. , 2012, Journal of the American Chemical Society.

[8]  E. Kramer,et al.  A modular strategy for fully conjugated donor-acceptor block copolymers. , 2012, Journal of the American Chemical Society.

[9]  Z. Bao,et al.  In situ hetero end-functionalized polythiophene and subsequent "click" chemistry with DNA. , 2012, Macromolecular rapid communications.

[10]  M. Thelakkat,et al.  Synthesis of Amphiphilic Rod–Coil P3HT-b-P4VP Carrying a Long Conjugated Block Using NMRP and Click Chemistry , 2012 .

[11]  C. Luscombe,et al.  Constructing Regioregular Star Poly(3-hexylthiophene) via Externally Initiated Kumada Catalyst-Transfer Polycondensation. , 2012, ACS macro letters.

[12]  T. Verbiest,et al.  End Group-Functionalization and Synthesis of Block-Copolythiophenes by Modified Nickel Initiators , 2011 .

[13]  T. Baumgartner,et al.  End-group functionalization of poly(3-hexylthiophene) as an efficient route to photosensitize nanocrystalline TiO2 films for photovoltaic applications. , 2011, ACS applied materials & interfaces.

[14]  J. Hao,et al.  Block copolymer containing poly(3-hexylthiophene) and poly(4-vinylpyridine): Synthesis and its interaction with CdSe quantum dots for hybrid organic applications , 2011 .

[15]  T. Verbiest,et al.  Influence of the Presence and Length of an Alkyl Spacer on the Supramolecular Chirality of Block Copoly(thiophene)s , 2011 .

[16]  Natalia V. Doubina,et al.  Steric Effects of the Initiator Substituent Position on the Externally Initiated Polymerization of 2-Bromo-5-iodo-3-hexylthiophene , 2011 .

[17]  P. Dubois,et al.  Stereocomplexed Materials Based on Poly(3-hexylthiophene)-b-poly(lactide) Block Copolymers: Synthesis by Organic Catalysis, Thermal Properties, and Microscopic Morphology , 2010 .

[18]  A. McNeil,et al.  Evidence for Ligand-Dependent Mechanistic Changes in Nickel-Catalyzed Chain-Growth Polymerizations , 2010 .

[19]  P. Dubois,et al.  Regioregular poly(3-hexylthiophene)-poly(ε-caprolactone) block copolymers: Controlled synthesis, microscopic morphology, and charge transport properties , 2010 .

[20]  Tomoya Higashihara,et al.  Synthesis of block copolymers consisting of poly(3-hexylthiophene) and polystyrene segments through ionic interaction and their self-assembly behavior , 2010 .

[21]  T. Verbiest,et al.  Incorporation of Different End Groups in Conjugated Polymers Using Functional Nickel Initiators , 2009 .

[22]  C. Luscombe,et al.  Externally initiated regioregular P3HT with controlled molecular weight and narrow polydispersity. , 2009, Journal of the American Chemical Society.

[23]  Jae Kwan Lee,et al.  Well-defined donor–acceptor rod–coil diblock copolymers based on P3HT containing C60: the morphology and role as a surfactant in bulk-heterojunction solar cells , 2009 .

[24]  Natalia V. Doubina,et al.  Effect of Initiators on the Kumada Catalyst-Transfer Polycondensation Reaction , 2009 .

[25]  M. Thelakkat,et al.  Tailor-made synthesis of poly(3-hexylthiophene) with carboxylic end groups and its application as a polymer sensitizer in solid-state dye-sensitized solar cells , 2009 .

[26]  Manabu Tanaka,et al.  Alternate network film of thiol group-terminated polythiophene and gold nanoparticle , 2007 .

[27]  T. Yokozawa,et al.  Catalyst-transfer polycondensation. mechanism of Ni-catalyzed chain-growth polymerization leading to well-defined poly(3-hexylthiophene). , 2005, Journal of the American Chemical Society.

[28]  R. D. Mccullough,et al.  Facile Synthesis of End-Functionalized Regioregular Poly(3-alkylthiophene)s via Modified Grignard Metathesis Reaction , 2005 .

[29]  N. Taniguchi.  Alkyl- or arylthiolation of aryl iodide via cleavage of the S-S bond of disulfide compound by nickel catalyst and zinc. , 2004, The Journal of organic chemistry.

[30]  Zhenan Bao,et al.  Synthesis and Characterization of Conjugated Mono- and Dithiol Oligomers and Characterization of Their Self-Assembled Monolayers , 2003 .

[31]  A. Ogawa,et al.  Facile S-alkyl thiocarbamate synthesis by a novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur , 2003 .

[32]  L. Lindoy.  Reactions involving metal complexes of sulphur ligands , 1969 .

[33]  A. Boukai,et al.  Oligo- and polythiophene/ZnO hybrid nanowire solar cells. , 2010, Nano letters (Print).

[34]  J. V. Dongen,et al.  End-group modification of regioregular poly(3-alkylthiophene)s , 2000 .