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Pyrrolo[3,4-c]pyrrole-1,3-dione Based Wide Band Gap Polymers for Polymer Solar Cells
Tamilavan, Vellaiappillai,Kim, Heewon,Kim, Seungmin,Cho, Shinuk,Jin, Youngeup,Jeong, Junghyun,Park, Sung Heum,Hyun, Myung Ho American Scientific Publishers 2017 Journal of Nanoscience and Nanotechnology Vol.17 No.8
<P>Four new alternating copolymers, P(CPD-T-DPPD), P(CPD-Se-DPPD), P(CPD-T-BDPPD) and P(CPD-Se-BDPPD), containing electron rich cyclopentadithiophene (CPD) and four different pyrrolo[ 3,4-c] pyrrole-1,3-dione (DPPD) derivatives (T-DPPD, Se-DPPD, T-BDPPD and Se-BDPPD) were prepared using Stille polymerization. The estimated optical band (E-g) gaps of the copolymers were 1.96 eV, 1.88 eV, 2.00 eV and 1.92 eV, respectively. The determined highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO) energy levels of the copolymers were -5.14 eV/-3.18 eV, -5.14 eV/-3.26 eV, -5.24 eV/-3.24 eV, and -5.24 eV/-3.32 eV, respectively. The polymer solar cells (PSCs) prepared with the configuration of ITO/PEDOT: PSS/copolymer: PC70BM/Al exhibited a maximum power conversion efficiency (PCE) of 0.63%, 1.01%, 0.18%, and 0.40%, respectively.</P>
Tamilavan, Vellaiappillai,Song, Myungkwan,Agneeswari, Rajalingam,Kim, Sangjun,Hyun, Myung Ho Korean Chemical Society 2014 Bulletin of the Korean Chemical Society Vol.35 No.4
New electron deficient acceptor-acceptor-acceptor type of monomer unit composed of weak electron accepting benzimidazole and relatively strong electron accepting benzothiadiazole derivatives namely 4,7-bis(6-bromo-1-(2-ethylhexyl)-1H-benzo[d]imidazol-2-yl)benzo[c][1,2,5]thiadiazole (BBB) was synthesized. The Stille polycondensation of the newly synthesized BBB monomer with electron donating 2,6-bis(trimethyltin)-4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene (BDT) afforded donor-acceptor-acceptor-acceptor type of polymer namely 2,6-(4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b']dithiophene)-alt-4,7-bis(1-(2-ethylhexyl)-1H-benzo[d]imidazol-2-yl)benzo[c][1,2,5]thiadiazole (PBDTBBB). The opto-electrical studies revealed that the absorption band of PBDTBBB appeared in the range of 300 nm-525 nm and its highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels were positioned at -5.18 eV and -2.84 eV, respectively. The power conversion efficiency (PCE) of the polymer solar cell (PSC) prepared from PBDTBBB:PC71BM (1:2 wt %) blend was 1.90%.
Tamilavan, Vellaiappillai,Sakthivel, Pachagounder,Li, Yinan,Song, Myungkwan,Kim, Chul-Hyun,Jin, Sung-Ho,Hyun, Myung Ho Wiley Subscription Services, Inc., A Wiley Company 2010 Journal of polymer science Part A, Polymer chemist Vol.48 No.14
<P>Two novel alternating π-conjugated copolymers, poly[2,8-(6,6′,12,12′-tetraoctyl-6,12-dihydroindeno-[1,2b]fluorene- alt-5(1-(2,6-diisopropylphenyl)-2,5-di(2-thienyl)pyrrole) (P1) and poly[2,8-(6,6′,12,12′-tetraoctyl-6,12-dihydroindeno-[1,2b]fluorene- alt-5(1-(p-octylphenyl)-2,5-di(2-thienyl)pyrrole) (P2), were synthesized via the Suzuki coupling method and their optoelectronic properties were investigated. The resulting polymers P1 and P2 were completely soluble in various common organic solvents and their weight-average molecular weights (M<SUB>w</SUB>) were 5.66 × 10<SUP>4</SUP> (polydispersity: 1.97) and 2.13× 10<SUP>4</SUP> (polydispersity: 1.54), respectively. Bulk heterojunction (BHJ) solar cells were fabricated in ITO/PEDOT:PSS/polymer:PC<SUB>70</SUB>BM(1:5)/TiO<SUB>x</SUB>/Al configurations. The BHJ solar cell with P1:PC<SUB>70</SUB>BM (1:5) has a power conversion efficiency (PCE) of 1.12% (J<SUB>sc</SUB>= 3.39 mA/cm<SUP>2</SUP>, V<SUB>oc</SUB>= 0.67 V, FF = 49.31%), measured using AM 1.5 G solar simulator at 100 mW/cm<SUP>2</SUP> light illumination. We fabricated polymer light-emitting diodes (PLEDs) in ITO/PEDOT:PSS/emitting polymer:polyethylene glycol (PEG)/Ba/Al configurations. The electroluminescence (EL) maxima of the fabricated PLEDs varied from 526 nm to 556 nm depending on the ratio of the polymer to PEG. The turn-on voltages of the PLEDs were in the range of 3–8 V depending on the ratio of the polymer to PEG, and the maximum brightness and luminance efficiency were 2103 cd/m<SUP>2</SUP> and 0.37 cd/A at 12 V, respectively. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3169–3177, 2010</P> <B>Graphic Abstract</B> <P>Two novel indenofluorene-based copolymers containing 2,5-bis(2-thienyl)-N-(4-octylphenyl)pyrrole or 2,5-bis(2-thienyl)-N-(2,6-diisopropylphenyl)pyrrole were prepared for bulk hetrojunction solar cells and polymer light-emitting diodes. <img src='wiley_img_2010/0887624X-2010-48-14-POLA24101-gra001.gif' alt='wiley_img_2010/0887624X-2010-48-14-POLA24101-gra001'> </P>
Tamilavan, Vellaiappillai,Roh, Kyung Hwan,Agneeswari, Rajalingam,Lee, Dal Yong,Cho, Shinuk,Jin, Youngeup,Park, Sung Heum,Hyun, Myung Ho The Royal Society of Chemistry 2014 Journal of Materials Chemistry A Vol.2 No.47
<P>As an effort to improve the photovoltaic properties of a highly efficient large band gap (2.11 eV) alternating copolymer, P(BDT-TDPPDT), comprised of electron rich benzodithiophene (BDT) and novel electron accepting pyrrole-based imide functionalized 4,6-bis(thiophen-2-yl)-2,5-dioctylpyrrolo[3,4-<I>c</I>]pyrrole-1,3-dione (TDPPDT) derivatives, we incorporated a relatively strong electron accepting thiophene-based imide functionalized thieno[3,4-<I>c</I>]pyrrole-4,6-dione (TPD) unit in its main chain<I>via</I>random copolymerization between BDT, TDPPDT and TPD units to give polymer P1. The incorporation of a TPD unit resulted in significant improvement in the optoelectrical and photovoltaic properties. P1 exhibits lower optical band gap (1.91 eV) and a deeper lowest unoccupied molecular orbital (LUMO) energy level compared to those of P(BDT-TDPPDT). The hole mobility of P1 was 3.66 × 10<SUP>−4</SUP>cm<SUP>2</SUP>V<SUP>−1</SUP>s<SUP>−1</SUP>and the PSC made with a simple device structure of ITO/PEDOT:PSS/P1:PC70BM(1 : 2.25 wt%) + 3 vol%/Al gave a maximum power conversion efficiency (PCE) of 7.03% with high photovoltaic parameters, such as an open-circuit voltage (<I>V</I>oc) of 0.87 V, a short-circuit current (<I>J</I>sc) of 11.52 mA cm<SUP>−2</SUP>and a fill factor (FF) of 70%. Interestingly, P1-based PSCs exhibited a high incident photon to current efficiency (IPCE) of a maximum of 78% at 410 nm and a more than 70% response between 370-590 nm. The PCE achieved in this study is the highest value reported thus far among PSCs made with random copolymers.</P>
Tamilavan, Vellaiappillai,Liu, Yanliang,Lee, Jihoon,Jung, Yun Kyung,Son, Semo,Jeong, Junghyun,Park, Sung Heum The Royal Society of Chemistry 2018 Journal of materials chemistry. C, Materials for o Vol.6 No.15
<P>A new alternating polymer P(BDTSi-DFBT), poly(4,8-bis(triisopropylsilylethynyl)-benzo[1,2-<I>b</I>:4,5-<I>b</I>′]dithiophene-<I>alt</I>-5,6-difluoro-4,7-bis(4-octylthiophen-2-yl)benzo[<I>c</I>][1,2,5]thiadiazole), was prepared <I>via</I> Stille polymerization. The determined absorption maximum and optical band-gap (<I>E</I>g) of P(BDTSi-DFBT) were 590 nm and 1.74 eV, respectively. The calculated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of P(BDTSi-DFBT) were −5.45 eV and −3.71 eV, respectively. The X-ray diffraction (XRD) analysis confirmed that P(BDTSi-DFBT) is a crystalline polymer. The binary-polymer solar cells, ITO/PEDOT:PSS/P(BDTSi-DFBT) : PC70BM (1 : 1.5 wt%) + 3 vol% DIO/Al, made from P(BDTSi-DFBT) gave a power conversion efficiency (PCE) of 5.02% with an open-circuit voltage (<I>V</I>oc) of 0.81 V, a short-circuit current (<I>J</I>sc) of 11.68 mA cm<SUP>−2</SUP>, and a fill factor (FF) of 53%. Conversely, the ternary-polymer solar cells, ITO/PEDOT:PSS/PTB7-Th : P(BDTSi-DFBT) : PC70BM (0.8 : 0.2 : 1.5 wt%) + 3 vol% DIO/Al, made with a synthesized medium band-gap P(BDTSi-DFBT) and low band-gap PTB7-Th, offered a maximum PCE of 10.05%, with a <I>V</I>oc of 0.79 V, a <I>J</I>sc of 17.92 mA cm<SUP>−2</SUP>, and a FF of 71%.</P>
Tamilavan, Vellaiappillai,Lee, Jihoon,Lee, Dal Yong,Agneeswari, Rajalingam,Jung, Yun Kyung,Jin, Youngeup,Jeong, Jung Hyun,Hyun, Myung Ho,Park, Sung Heum The Royal Society of Chemistry 2018 New journal of chemistry Vol.42 No.14
<P>In this study, two new pyrrolo[3,4-<I>c</I>]pyrrole-1,3-dione (PPD)-based polymers (P3 and P4) incorporating a 2-octyldodecyl (branched alkyl) group on the pyrrole nitrogen of the PPD unit were prepared. Their properties were briefly compared to those of the structurally quite similar PPD-based polymers (P1 and P2) with an <I>n</I>-octyl (linear alkyl) group on the PPD unit, in order to understand the importance of the pyrrole <I>N</I>-alkyl group. The calculated optical band gaps (<I>E</I>g) and highest occupied molecular orbital energy levels of P3 and P4 were found to be around ∼0.1 eV higher and deeper, respectively, compared to those of the respective linear alkylated polymers P1 and P2. The maximum power conversion efficiency (PCE) obtained for the polymer solar cells made by using P3 or P4:PC70BM blends without any additive was around ∼2%, which was quite similar to that of the PSCs made using P1 or P2:PC70BM blends. However, P3 and P4 exhibited a notably lower PCE than that of P1 and P2, respectively, when the polymer solar cells were created with an additive. This study confirmed that the alkyl substituent on the pyrrole nitrogen of the PPD unit significantly affects the properties of the resulting polymer.</P>
Tamilavan, Vellaiappillai,Shin, Insoo,Agneeswari, Rajalingam,Liu, Yanliang,Jung, Yun Kyung,Lee, Bo Ram,Jin, Youngeup,Jeong, Jung Hyun,Ho Hyun, Myung,Park, Sung Heum Elsevier 2019 Journal of photochemistry and photobiology Chemist Vol.371 No.-
<P><B>Abstract</B></P> <P>A 2,5-bis(2-thienyl)pyrrole (TPT)-based new monomer unit incorporating the electron-withdrawing 1-decanone (ketone) at the 3- and 4-positions of the pyrrole unit of TPT was prepared. The resulting keto-functionalized TPT unit (≈TPTK) was polymerized with distannyl derivatives of 4,8-bis(5-(2-ethylhexyl)thiophen-2-yl)benzo[1,2-<I>b</I>:4,5-<I>b</I>′]dithiophene (BDTT), 4,7-bis(thiophen-2-yl)benzo[<I>c</I>][1,2,5]thiadiazole (DTBT), and 3,6-bis(thiophen-2-yl)-2,5-dioctylpyrrolo[3,4-<I>c</I>]pyrrole-1,4(2H,5H)-dione (DKPP), to obtain three new polymers (<B>P(BDTT-TPTK), P(DTBT-TPTK)</B> and <B>P(DKPP-TPTK))</B>, respectively. The photophysical, electrochemical, and energy conversion efficiency of the TPTK-based polymers were thoroughly studied and compared with those of structurally similar polymers (P(BDTT-TPTI), P(DTBT-TPTI), and P(DKPP-TPTI)) incorporating an imide-functionalized TPT unit (≈ TPTI). Overall, the TPTK-based polymers showed a higher band-gap (<I>E<SUB>g</SUB> </I> ≈ 2.42 eV, 1.92 eV, and 1.42 eV), deeper highest occupied molecular orbital (HOMO ≈ −5.58 eV, −5.48 eV, and −5.31 eV, respectively) energy levels and lower carrier mobilities than those of the corresponding TPTI-based polymers. These combined effects led to relatively poor solar to electrical energy conversion efficiency for TPTK-based polymers compared to those of TPTI-based polymers.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Keto-functionalized 2,5-bis(2-thienyl)pyrrole (TPTK)-based new polymers prepared. </LI> <LI> The opto-electrical and photovoltaic properties of new polymers elaborately studied. </LI> <LI> The properties are compared with those of imide-functionalized (TPTI) polymers. </LI> <LI> TPTK-polymers showed higher band-gap and lower mobility than TPTI-polymers. </LI> <LI> TPTK-polymers showed less PCE than TPTI-polymers. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>