Poly(3-dodedyl-2,5-thienylenevinylene)s from the Stille coupling and the Horner–Emmons reaction

Zhang, Cheng; Matos, Taina D.; Li, Rui; Sun, Sam-Shajing; Lewis, Jason; Zhang, Jian; Jiang, Xiran

doi:10.1039/b9py00324j

Cited by 41 publications

(64 citation statements)

References 16 publications

(23 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The shoulder peak at 701 nm could be attributed to the O-stacking of the planarized individual polymer chains, because the peak is not seen in the absorption spectrum of a hot solution (oDCB at 150°C) of the polymers. 18 The optical E g values of PPhDOTV and PPhDOTFV determined from the absorption onset of the film state were almost the same, 1.66 eV. The HOMO levels of PPhDOTV and PPhDOTFV estimated by photoelectron yield spectroscopy were ¹5.14 and ¹5.34 eV, respectively, and are summarized in Fig.…”

Section: Synthesis and Fundamental Properties Of Pphdotv Andmentioning

confidence: 77%

Organic Photovoltaics Based on Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s

2017

View full text Add to dashboard Cite

Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s with a fluorine substituent at the phenylene moiety (PPhDOTFV) and without the substituent (PPhDOTV) were synthesized by Stille coupling polymerization. They exhibited good solubility in common organic solvents owing to a branched alkyl chain at the phenylene moiety and a narrow optical bandgap of 1.66 eV due to an increased conjugated length caused by the vinylene bridge. Both the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of PPhDOTFV were 0.2 eV deeper than those of PPhDOTV. Organic photovoltaic cells (OPVs) using PPhDOTV:PC 70 BM exhibited a short-circuit current density (J sc ) of 3.30 mA cm , an open-circuit voltage (V oc ) of 0.52 V, and a power conversion efficiency of 0.91%, as compared to 1.62 mA cm −2 , 0.68 V, and 0.45%, respectively, for OPVs using PPhDOTFV:PC 70 BM. The J sc value of PPhDOTV-based OPVs was higher than that of PPhDOTFV-based OPVs because of a large LUMO energy offset between PPhDOTV and PC 70 BM. On the other hand, the V oc value of PPhDOTV-based OPVs was lower than that of PPhDOTFV-based OPVs because of a small energy difference between the HOMO level of PPhDOTV and the LUMO level of PC 70 BM.

show abstract

Section: Synthesis and Fundamental Properties Of Pphdotv Andmentioning

confidence: 77%

Organic Photovoltaics Based on Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s

2017

View full text Add to dashboard Cite

show abstract

“…The polymers did not show any peak corresponding to glass transition, crystallization or melting. This typical feature for amorphous polymers is well supported by the absence of any corresponding peak in their thin-film Xray diffraction (XRD) pattern (see Figure S8, Supporting Information) unlike P3DSV 22 or HE-C12-PTV, 8 which exhibited physical transitions in DSC. It could be attributed to the increasing amorphous nature and rigidity of the polymer main chain due 3,4-cyclopentane substitution.…”

Section: ■ Introductionmentioning

confidence: 96%

Synthesis of Solution-Processable Poly(cyclopenta[c]selenylvinylene) and Its Charge Transport Properties: Comparative Study with the Thiophene Analogue

et al. 2013

View full text Add to dashboard Cite

We report here the synthesis and characterization of 5,5-bis(dodecyloxymethyl)-5,6-dihydro-4H-cyclopenta[c]selenophene (DCPS) and its characterization by single crystal X-ray diffraction technique. In continuation to this, two new solution-processable copolymers PDCPSV and P D C P T V , c o m p r i s i n g o f D C P S a n d 5 , 5 -b i s -(dodecyloxymethyl)-5,6-dihydro-4H-cyclopenta[c]thiophene (DCPT), respectively, in combination with vinylene unit were synthesized, characterized and compared on the basis of their physical, optical and electronic properties. We have successfully introduced vinylene linkage between two consecutive DCPS or DCPT units in the polymer main chain that resulted in low band gap and oxidatively stable polymers. The 3,4-cyclopentane substitution on thiophene and selenophene affords the planarity to the resulting polymers and the question of regioregularity does not arise in the polymer chain in contrast to the 3-alkyl substitution. PDCPSV showed a p-type mobility of 5.6 × 10 −3 cm 2 V −1 s −1 , whereas PDCPTV showed 3.8 × 10 −3 cm 2 V −1 s −1 . The polymers were further characterized by GPC, TGA, DSC, thinfilm XRD, and cyclic voltammetry (CV).

show abstract

“…These observations are consistent with previous reports on PTVs obtained through ADMET and indicate regiorandom nature of the P3DSV structure, different from the regioregular polymers synthesized from Horner-Emmons and Stille coupling reactions. 12,32 In order to prepare the copolymer and to avoid large difference in monomer polymerization rates, …”

mentioning

confidence: 99%

Synthesis and Characterization of Poly(selenylene vinylene) and Poly(selenylene vinylene)-co-Poly(thienylene vinylene) through Acyclic Diene Metathesis (ADMET) Polymerization

Zhang

Qin

2015

ACS Macro Lett.

View full text Add to dashboard Cite

We report the synthesis and characterization of poly(3-decylselenylene vinylene) (P3DSV) homopolymers and poly(3-decylselenylene vinylene)-co-poly(3-decylthienylene vinylene) (P3DSV-co-P3DTV) copolymers through acyclic diene metathesis (ADMET) polymerization techniques. The obtained polymers were fully characterized. P3DSV was found to possess reduced crystallinity and a smaller bandgap of about 1.6 eV, compared with those of poly(3-decylthienylene vinylene) (P3DTV) analogs. P3DSV-co-P3DTV shows electronic properties between those of the corresponding homopolymers and distinctly different from those of simple blends of the two homopolymers. Our methodology provides a new way to control the physical and electronic properties of low bandgap poly(arylene vinylene)s (PAVs). C onjugated polymers (CPs) have found widespread applications in solution processed thin film electronic devices. 1 CPs possessing low electronic bandgaps are especially attractive in optoelectronic devices including organic photovoltaics (OPVs). 2−4 Among a plethora of examples, low bandgap poly(thienylene vinylene) (PTV) derivatives have attracted increasing attention due to high charge mobilities, 5 environmental and thermal stability, 1 and recently discovered singlet fission processes. 6 Various synthetic methods have been developed and refined over the years for PTV preparation, including earlier examples involving Gilch-type reactions and elimination from soluble polymeric precursors, 7−9 McMurry coupling, and Wittig-type reactions of aldehyde-containing monomers, 10−12 transition metal catalyzed cross-coupling reactions, 13−15 and, more recently, acylic diene metathesis (ADMET) polymerization of thiophene monomers bearing double bonds at 2,5-positions. 16−21 Applications of these soluble PTVs have been attempted in OPV devices, but only low to moderate device efficiencies have been obtained. 22−24 Despite morphology controllability issues, 25 extremely short exciton lifetimes in PTVs due to ultrafast nonradiative decay rates have been ascribed as the main reasons for low OPV performances. 6,26 Thus, in order for PTVs to be more applicable for OPV and other optoelectronic devices, structural modifications and subsequent optimization in physical/ electronic properties are necessary.One such structural modification is to replace the sulfur atoms in PTVs with selenium, the next heavier element in group 16, generating poly(selenylene vinylene)s (PSVs). The larger sizes, enhanced polarizability, and stronger spin−orbit coupling effects of selenium atoms are expected to result in significantly different physical/electronic properties over their sulfur counterparts. 2 7 − 2 9 Fo r i nstance, poly(3-alkylselenophene)s (P3ASs) have been shown to possess smaller bandgaps and lower ionization potentials than that of the well-studied poly(3-alkylthiophene)s (P3ATs). 30,31 Heeney et al. and Zade et al. recently reported the preparation of alkyland cycloalkyl-substituted PSV derivatives, respectively, through palladium-catalyzed Stille coupling reactions...

show abstract

Poly(3-dodedyl-2,5-thienylenevinylene)s from the Stille coupling and the Horner–Emmons reaction

Cited by 41 publications

References 16 publications

Organic Photovoltaics Based on Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s

Organic Photovoltaics Based on Poly(3,4-phenylenedioxy-2,5-thienylenevinylene)s

Synthesis of Solution-Processable Poly(cyclopenta[c]selenylvinylene) and Its Charge Transport Properties: Comparative Study with the Thiophene Analogue

Synthesis and Characterization of Poly(selenylene vinylene) and Poly(selenylene vinylene)-co-Poly(thienylene vinylene) through Acyclic Diene Metathesis (ADMET) Polymerization

Contact Info

Product

Resources

About