An ADMET Route to Low-Band-Gap Poly(3-hexadecylthienylene vinylene): A Systematic Study of Molecular Weight on Photovoltaic Performance

Speros, Joshua C.; Paulsen, Bryan D.; White, Scott P.; Wu, Yanfei; Jackson, Elizabeth A.; Slowinski, Bradley S.; Frisbie, C. Daniel; Hillmyer, Marc A.

doi:10.1021/ma3000434

Cited by 42 publications

(46 citation statements)

References 66 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[79] A low band-gap of 1.6 eV, determined by solid-state UV/Vis spectroscopy and consistent with cyclic voltammetry data, suggests a greater tion [81] in the presence of third-generation Grubbs catalysts bearing bromopyridine ligands, [82] which exhibit remarkable activity in these processes. …”

Section: Alkene Metathesissupporting

confidence: 63%

Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

et al. 2014

View full text Add to dashboard Cite

Bequeme Routine: Mehrlagige dünne Polymerfilme wurden durch Elektrophorese auf in Agarose immobilisierten Partikeln angeordnet. Anschließendes Entfernen des Kerns führte zu robusten Kapseln mit unterschiedlichen Polymerzusammensetzungen (siehe Fluoreszenzbild). Dieser Ansatz ermöglicht den vielseitigen und routinemäßigen Aufbau von nano‐ und mikroskaligen Kapseln sowie beschichteten Partikeln in sehr wenigen Prozessschritten.

show abstract

Section: Alkene Metathesissupporting

confidence: 63%

Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

et al. 2014

View full text Add to dashboard Cite

show abstract

“…The synthesis of the polymers were carried out using palladium-catalyzed Stille coupling between monomer 1,3-dibromo-5-(2-octyldodecyl)thieno [3,4-c]pyrrole-4,6-dione (TPD), 2,5-dibromothiophene (7), and (E)-1,2-bis(tributylstannyl)-ethane (8), as shown in Scheme 2. Under the protection of nitrogen, monomers were dissolved in chlorobenzene.…”

Section: General Procedures Of Polymerizationmentioning

confidence: 99%

“…8,21 This can be attributed to the lower HOMO levels of the polymers due to the electron-withdrawing imide substituents. The PCE (0.23%) of the PSCs based on P24 was close to that of typical PTVs, [17][18][19][20][21] indicating that one-third imide substitution of the thiophene units in P24 influences the photovoltaic performance of the polymers very little.…”

Section: Photovoltaic Propertiesmentioning

confidence: 99%

“…[1][2][3][4][5][6][7] Poly(thienylene vinylene) derivatives (PTVs) is an important class of low-bandgap polymers. [8][9][10][11][12][13][14][15] PTVs have already proven to have broad absorption spectra (bandgap ca. 1.5-1.8 eV) combining with high hole mobility (up to 0.2 cm 2 V 21 s 21 ), 16 which makes them attractive candidates for photovoltaic applications.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and electronic energy‐level regulation of imide‐fused poly(thienylene vinylene) derivatives

Wang

Gao

Wang

et al. 2013

J. Polym. Sci. Part A: Polym. Chem.

View full text Add to dashboard Cite

A series of novel poly(thienylene vinylene) derivatives (PTVs), P20-P24, with imide substituents were designed and synthesized by palladium-catalyzed Stille coupling polymerization, wherein the imide substituent density was decreased gradually, which allowed us to explicitly study the effect of electron-deficient substituent on the optical, electrochemical, and photovoltaic properties of the PTVs. All of the four polymers showed broad absorption bands with optical bandgaps between1.66 and 1.78 eV. By reducing density of electron-deficient imide group, the LUMO energy levels of the polymers could be tuned gradually from 23.75 to 23.

show abstract

“…The C16 monomer was prepared following a previous literature report 26 in 68% overall yield with a Z/E ratio of 83:17. The synthesis of OC16 began by treating 3-bromothiophene with the sodium alkoxide of 1-hexadecanol in the presence of copper iodide.…”

mentioning

confidence: 99%

Band Gap and HOMO Level Control in Poly(thienylene vinylene)s Prepared by ADMET Polymerization

et al. 2012

Self Cite

View full text Add to dashboard Cite

Three dipropenyl monomers were prepared for ruthenium-catalyzed acyclic diene metathesis (ADMET) polymerization. Homopolymerization afforded three poly-(thienylene vinylene)s (PTVs) with distinct optoelectronic properties. Binary combinations of the monomers over a range of compositions gave three series of copolymer samples with tunable HOMO levels and band gaps. The utility of this method was further demonstrated by the preparation of a stoichiometric terpolymer. Polymers were characterized by 1 H NMR spectroscopy, size-exclusion chromatography, ultraviolet−visible spectroscopy, and cyclic voltammetry. This copolymerization approach effectively demonstrates the ability of ADMET polymerization to prepare conjugated copolymers with tuned optoelectronic properties that span a broad composition window.T he ability to tune the properties of conjugated polymers (CPs) through chemical modification has allowed for their integration in sensors, 1 organic light-emitting diodes, 2 field-effect transistors, 3 and organic photovoltaics (OPVs). 4 OPVs are of particular interest because cost-effective solution processing techniques can be used for their preparation. Stateof-the-art OPV power conversion efficiencies now lie in the 7− 9% range 5−8 as a result of both device optimization and the development of low band gap CPs typically having a perfectly alternating sequence of donor and acceptor (D-A) monomeric units. 9 Low band gap CPs are desirable because they often afford efficient and broad absorption of the solar spectrum. Systematic tuning of the band gap in a homologous set of CP materials can be ideally used to optimize OPV performance. However, such tunability can be synthetically difficult to achieve in conventional D-A polymers. Here we describe an approach to tunable energy levels based on copolymerization of structurally and electronically distinct monomers.Few researchers have explored statistical copolymerization methods for the preparation of CPs. Unlike the alternating D-A approach, 10 a primary advantage of this strategy is the ability to probe nonstoichiometric monomer combinations instead of the 1:1 composition imposed by an alternating architecture. Some of the earliest examples of random CPs were aimed at tuning photoluminescence properties and were prepared by Yamamoto coupling of various dibromo monomers. 11,12 However, a broad composition range was not studied. More recent examples of random CPs make use of palladium-catalyzed Suzuki and Stille coupling strategies. 13,14 These routes require lengthy syntheses of, for example, one diboronic ester/ditin monomer and two dibromo monomers. Additionally, given the alternating nature of these polymerizations, only half of the composition window is accessible. Recently, Thompson and coworkers built on the utility of this approach by demonstrating "semi-random" CPs using 2-bromo-5-trimethyltin-3-hexylthiophene, 2,5-bis(trimethyltin)-thiophene, and 4,7-dibromo-2,1,3-benzothiadiazole or dibromo-bisthiophene-diketopyrrolopyrrole monomers and Stille coupling condi...

show abstract

An ADMET Route to Low-Band-Gap Poly(3-hexadecylthienylene vinylene): A Systematic Study of Molecular Weight on Photovoltaic Performance

Cited by 42 publications

References 66 publications

Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

Organometallic Approaches to Conjugated Polymers for Plastic Solar Cells: From Laboratory Synthesis to Industrial Production

Synthesis and electronic energy‐level regulation of imide‐fused poly(thienylene vinylene) derivatives

Band Gap and HOMO Level Control in Poly(thienylene vinylene)s Prepared by ADMET Polymerization

Contact Info

Product

Resources

About