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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,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,Kim, A-Young,Lee, Hojeong,Kim, Hye-Bin,Kim, Sangjun,Kang, Misook,Hyun, Myung Ho Elsevier 2014 Synthetic metals Vol.191 No.-
To investigate the N-aryl group influences on the optical, electrochemical and photovoltaic properties of thiophene-(N-aryl)pyrrole-thiophene (N-Aryl TPT)-based dyes, two new dyes (TPTDYE 3 and TPTDYE 4) were prepared by attaching the electron donating and non-planar 4'-(N,N-diphenylamino)biphenyl or 3-fluoro-4'-(N,N-diphenylamino)biphenyl group on the pyrrole nitrogen of the thiophene-pyrrole-thiophene (TPT) unit and the electron accepting cyanoacrylic acid group at the 3-position of pyrrole unit. In addition, another two new dyes (TPTDYE 5 and TPTDYE 6) were obtained by introducing two more triphenylamine groups on the both side of the TPT unit of TPTDYE 3 and TPTDYE 4, respectively. The shapes of the dyes are found to be similar to umbrella, since three electron donor groups are placed around the cyanoacrylic acid group positioned at middle of the dyes. The absorption spectra of dyes TPTDYE 5 and TPTDYE 6 were found to be relativity broad (similar to 300-475 nm) and red shifted compared to the absorption spectra (similar to 300-425 nm) of dyes TPTDYE 3 and TPTDYE 4. The electrochemical studies indicate that the HOMO energy levels of the non-fluorinated dyes (TPTDYE 3 and TPTDYE 5) were slightly deeper than fluorinated dyes (TPTDYE 4 and TPTDYE 6). The dye sensitized solar cells (DSSCs) prepared with TPTDYE 5 with and without coadsorbent offered a maximum energy conversion efficiency of 4.02% and 3.42%, respectively. (C) 2014 Elsevier B.V. All rights reserved.
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,Lee, Jihoon,Agneeswari, Rajalingam,Jung, Yun Kyung,Jin, Youngeup,Jeong, Jung Hyun,Hyun, Myung Ho,Park, Sung Heum Elsevier 2018 Organic Electronics Vol.63 No.-
<P><B>Abstract</B></P> <P>The conventional polymerization of 2,5-bis(trimethylstannyl)thiophene (T) or 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene (Tt) with 4,6-bis(5-bromothiophen-2-yl)-5-octyl-2-(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,3(2H,5H)-dione (TPPDT) afforded new alternating polymers, namely <B>P(T-TPPDT)</B> or <B>P(Tt-TPPDT)</B>, respectively. Both <B>P(T-TPPDT)</B> and <B>P(Tt-TPPDT)</B> exhibited similar thermal stabilities (5% weight loss at around 420 °C) and absorption maxima (<I>λ</I> <SUB>max</SUB> ≈ 515 nm) as films. The absorption bands of <B>P(T-TPPDT)</B> and <B>P(Tt-TPPDT)</B> extend between 300 and 620 nm, with optical band gaps (<I>E</I> <SUB> <I>g</I> </SUB>s) of 2.02 eV and 2.00 eV, respectively. The highest-occupied/lowest-unoccupied molecular-orbital energies of <B>P(Tt-TPPDT)</B> (HOMO/LUMO: −5.35 eV/–3.33 eV) were found to be somewhat higher than those of <B>P(T-TPPDT)</B> (HOMO/LUMO: −5.31 eV/–3.31 eV). Organic solar cells (OSCs) prepared using 1:1.5 (w/w) <B>P(T-TPPDT)</B>:PC<SUB>70</SUB>BM or <B>P(Tt-TPPDT)</B>:PC<SUB>70</SUB>BM (PC<SUB>70</SUB>BM = [6,6]-phenyl C<SUB>70</SUB> butyric acid methyl ester) blends provided power-conversion efficiencies (<I>PCE</I>s) of 3.50% or 4.71%, respectively. On the other hand, OSCs prepared with 1:1 (w/w) <B>P(T-TPPDT)</B>:ITIC or <B>P(Tt-TPPDT)</B>:ITIC (ITIC = 3,9-bis(2-methylene-(3-(1,1-dicyanomethylene)indanone))-5,5,11,11-tetrakis(4-hexylphenyl)dithieno[2,3-d:2′,3′-d’]-s-indaceno[1,2-b:5,6-b’]dithiophene) blends exhibited improved <I>PCE</I>s of 5.32% or 6.35%, respectively.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Two new polymers, <B>P(T-TPPDT)</B> and <B>P(Tt-TPPDT)</B>, were prepared. </LI> <LI> The optical band gaps were 2.02 eV and 2.00 eV. </LI> <LI> The HOMO/LUMO levels were −5.35 eV/‒3.33 eV and −5.31 eV/‒3.31 eV. </LI> <LI> The polymer:PC<SUB>70</SUB>BM blends offered a <I>PCE</I> of 3.50% and 4.71%. </LI> <LI> The polymer:ITIC blends provided a <I>PCE</I> of 5.32% and 6.35%. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>
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>