Synthesis and photovoltaic properties of 1-(2,6-diisopropylphenyl)-2,5-di(2-thienyl)pyrrole-based low-bandgap polymers

“…As expected, the HOMO energy levels of the polymers P(BDT-TDPPDT) and P(BDTT-TDPPDT) were found to be 0.2-0.4 eV deeper than 10 those of TPT-based polymers incorporating TPT as the donor unit. [22][23][24][25][26][27][28][29] Fig. 1 Structures of known polymers P(BDT-TDPPDT), P(BDTT-TDPPDT) and new polymers prepared in this study.…”

Section: Introductionmentioning

confidence: 99%

“…Although, all polymers showed poor photovoltaic performances (~1-2%) due mainly to the lower open circuit voltage (V oc ~ 0.4-0.5 V) and fill factor (FF ~ 30-40%). [22][23][24][25][26][27][28][29] The V oc and FF are dependent mainly on the highest occupied molecular orbital (HOMO) energy level and 70 carrier mobility of electron donating polymers. In an effort to lower the HOMO level as well as to improve the mobility of…”

mentioning

confidence: 99%

Modulation of the properties of pyrrolo[3,4-c]pyrrole-1,4-dione based polymers containing 2,5-di(2-thienyl)pyrrole derivatives with different substitutions on the pyrrole unit

et al. 2015

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In this study, four new pyrrolo [3,4-c]pyrrole-1,4-dione (DKPP)-based polymers, P(DKPP-TPTH), P(DKPP-TPTE), P(DKPP-TPTA), and P(DKPP-TPTI), containing N-alkyl-2,5-di(2-thienyl)pyrrole (TPT) derivatives with four different substituents such as hydrogen, ester, amide, and imide groups on the 10 3,4-position of the pyrrole unit were prepared to tune the properties of the polymers. Opto-electrical studies showed that the incorporation of electron withdrawing substituents such as ester, amide and imide groups instead of hydrogen on the pyrrole backbone of the polymers increased the band gaps significantly from 1.31 eV to 1.42 eV, 1.37 eV and 1.37 eV, respectively, and reduced the highest occupied/lowest unoccupied molecular orbital (HOMO/LUMO) energy levels from -4.96 eV/-3.65 eV to -5.24 eV/-3.82 15 eV, -5.17 eV/-3.80 eV and -5.35 eV/-3.98 eV, respectively. Organic field effect transistors (OFETs) made from these polymers indicated that the incorporation of electron withdrawing functional groups on the polymer backbone reduced the hole mobility. Polymer solar cells (PSCs) prepared with the polymers as an electron donor offered higher power conversion efficiency (PCE) for the polymer containing hydrogen on TPT backbone, but the polymers incorporating electron withdrawing substituents on the TPT 20 backbone showed a significantly higher open circuit voltage (V oc ) though the PCE was relatively lower. 30 reported for PSCs over the last decade. Note that the polymer and fullerene derivatives used in the photoactive layer of PSCs, the device structure and its preparation conditions are crucial factors determining the performance of PSCs. In this instance, chemists are looking forward to developing highly efficient donor or 35 acceptor materials and physicists are working more on the device optimization of PSCs to improve the PCE further. Currently, single junction PSCs made from single donor and acceptor 50 materials offer the maximum PCE in the range of 8-9.5%, 13-18 whereas multijunction or tandem PSCs prepared with two different donor and acceptor materials provide a relatively higher PCE of 9-11.5%. 1,[19][20][21] Since 2010, the authors have been involved in the preparation 55 of highly efficient 2,5-di(2-thienyl)pyrrole (TPT)-based polymeric donor materials for PSCs. [22][23][24][25][26][27][28][29] In the beginning of these studies, TPT was utilized as an electron donor unit and TPT-based polymers containing electron rich indenofluorene, 22 2,5-dioctyloxyphenylene 23 and 3-octylthiophene 23 or electron 60 accepting benzothiadiazole, 24-26 thiophene-benzothiadiazolethiophene (TBT), 27,28 and thiadiazoloquinoxaline (DQ) 29 were developed for PSCs. The opto-electrical and photovoltaic studies showed that the properties of TPT-based polymers varied considerably according to the electron rich or deficient units 65 incorporated in their main chain. Although, all polymers showed poor photovoltaic performances (~1-2%) due mainly to the lower open circuit voltage (V oc ~ 0.4-0.5 V) and fill factor (FF ~ 30-40%). [22][23][2...

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“…In our laboratory, we have been interested in the preparation of pyrrole‐based polymers for PSCs . Recently, a novel pyrrole‐based imide‐functionalized electron accepting unit, 4,6‐dibromo‐2,5‐dioctylpyrrolo[3,4‐c]pyrrole‐1,3(2H,5H)‐dione (DPPD), was designed and synthesized, and then polymerized with electron‐rich dithiophenepyrrole (DTP) .…”

Section: Introductionmentioning

confidence: 99%

Pyrrolo[3,4-c]pyrrole-1,3-dione-based large band gap polymers containing benzodithiophene derivatives for highly efficient simple structured polymer solar cells

Tamilavan

Roh

Agneeswari

et al. 2014

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

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Pyrrolo[3,4‐c]pyrrole‐1,3(2H,5H)‐dione (DPPD)‐based large band gap polymers, P(BDT‐TDPPDT) and P(BDTT‐TDPPDT), are prepared by copolymerizing electron‐rich 4,8‐bis(2‐ethylhexyloxy)benzo[1,2‐b:4,5‐b′]dithiophene (BDT) or 4,8‐bis(5‐(2‐ethylhexyl)thiophen‐2‐yl)benzo[1,2‐b:4,5‐b′]dithiophene (BDTT) unit with novel electron deficient 2,5‐dioctyl‐4,6‐di(thiophen‐2‐yl)pyrrolo[3,4‐c]pyrrole‐1,3(2H,5H)‐dione (TDPPDT) unit. The absorption bands of polymers P(BDT‐TDPPDT) and P(BDTT‐TDPPDT) cover the region from 300 to 600 nm with an optical band gap of 2.11 eV and 2.04 eV, respectively. The electrochemical study illustrates that the highest occupied/lowest unoccupied molecular orbital energy levels of P(BDT‐TDPPDT) and P(BDTT‐TDPPDT) are −5.39 eV/−3.28 eV and −5.44 eV/−3.40 eV, respectively. The single layer polymer solar cell (PSC) fabricated with a device structure of ITO/PEDOT:PSS/P(BDT‐TDPPDT) or P(BDTT‐TDPPDT):PC70BM+DIO/Al offers a maximum power conversion efficiency (PCE) of 6.74% and 6.57%, respectively. The high photovoltaic parameters such as fill factor (∼72%), open circuit voltage (Voc, ∼0.90 V), incident photon to collected electron efficiency (∼76%), and PCE obtained for the PSCs made from polymers P(BDT‐TDPPDT) and P(BDTT‐TDPPDT) make them as promising large band gap polymeric candidates for PSC application. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 3564–3574

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Synthesis and photovoltaic properties of 1-(2,6-diisopropylphenyl)-2,5-di(2-thienyl)pyrrole-based low-bandgap polymers

Cited by 13 publications

References 50 publications

New air-stable aromatic polyazomethines with triphenylamine or phenylenevinylene moieties towards photovoltaic application

New air-stable aromatic polyazomethines with triphenylamine or phenylenevinylene moieties towards photovoltaic application

Modulation of the properties of pyrrolo[3,4-c]pyrrole-1,4-dione based polymers containing 2,5-di(2-thienyl)pyrrole derivatives with different substitutions on the pyrrole unit

Pyrrolo[3,4-c]pyrrole-1,3-dione-based large band gap polymers containing benzodithiophene derivatives for highly efficient simple structured polymer solar cells

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