1000623-95-9Relevant academic research and scientific papers
Synthesis and Spectroscopic Investigation of Diketopyrrolopyrrole - Spiropyran Dyad for Fluorescent Switch Application
Doddi, Siva,Narayanaswamy,Ramakrishna, Bheerappagari,Singh, Surya Prakash,Bangal, Prakriti Ranjan
, p. 1939 - 1949 (2016)
We report the synthesis and characterization of a new fluorescent dyad SP-DPP-SP(9) via efficient palladium-catalyzed Sonogashira coupling of prop-2-yn-1-yl 3-(3′,3’dimethyl-6-nitrospiro[chromene-2,2′-indolin]-1′-yl)propanoatespiropyran, SP(8), a well known photochromic accepter, with 3,6-bis(5-bromothiophen-2-yl)-2,5-bis((R)-2-ethylhexyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, DPP(4), a highly fluorescent donor. Under visible light exposure the SP unit is in a closed hydrophobic form, whereas under UV irradiation it converts to a polar, hydrophilic open form named Merocyanine (MC), which is responsible for functioning of photo-switch application. The photochemistry pertaining to fluorescence switch, ‘on/off’ behaviour, of model dyad SP-DPP-SP(9) is experimentally analyzed in solution as well as in solid state in polymer matrices by photoluminescence(PL) and absorption spectroscopy. After absorption of UV light the spiropyran unit of the dyad under goes the rupture of the spiro C-O bond leading to the formation of MC. The absorption band of MC fairly overlaps to the fluorescence of DPP unit resulting quenching of fluorescence via fluorescence resonance energy transfer from exited DPP unit to ground state MC. In contrary, the fluorescence of DPP is fully regained upon transformation of MC to SP by exposure to visible light or thermal stimuli. Hence, the fluorescence intensity of dyad 9 is regulated by reversible conversion among the two states of the photochromic spiropyran units and the fluorescence resonance energy transfer (FRET) between the MC form of SP and the DPP unit. Conversely, these scrutiny of the experiment express that the design of dyad 9 is viable as efficient fluorescent switch molecule in many probable commercial applications, such as, logic gates and photonic and optical communications.
Synthesis and characterization of a narrow-bandgap polymer containing alternating cyclopentadithiophene and diketo-pyrrolo-pyrrole units for solar cell applications
Chen, Guan-Yu,Chiang, Chien-Ming,Kekuda, Dhananjay,Lan, Shang-Che,Chu, Chih-Wei,Wei, Kung-Hwa
, p. 1669 - 1675 (2010)
We have synthesized a narrow-bandgap conjugated polymer (PCTDPP) containing alternating cyclopentadithiophene (CT) and diketo-pyrrolo-pyrrole (DPP) units by Suzuki coupling. This PCTDPP exhibits a low band gap of 1.31 eV and a broad absorption band from 350 to 1000 nm, which allows it to absorb more available photons from sunlight. A bulk heterojunction polymer solar cell incorporating PCTDPP and C70 at a blend ratio of 1:3 exhibited a high short-circuit current of 10.87 mA/cm2 and a power conversion efficiency of 2.27%.
Air-stable ambipolar organic field-effect transistors based on naphthalenediimide-diketopyrrolopyrrole copolymers
Wang, Ping,Li, Hui,Gu, Chunling,Dong, Huanli,Xu, Zhenzhen,Fu, Hongbing
, p. 19520 - 19527 (2015)
Two air-stable polymeric semiconductors were rationally designed and synthesized, namely PNDI-DPP and PNDI-T(DPP)T, containing naphthalenediimide (NDI) units and diketopyrrolopyrrole (DPP). The coplanar thiophene-substituted DPP moieties act as donors rather than acceptors, even though DPP is an electron-deficient core. In a bottom-gate/top-contact device architecture, the effect of changing the number of thiophene linkers on the performance of the two completely different OFETs was investigated. PNDI-T(DPP)T presented unipolar p-type behaviour with an average hole mobility of 0.02 cm2 V-1 s-1, while PNDI-DPP exhibited ambipolar transport with average electron and hole mobilities of 5.7 × 10-3 and 1.6 × 10-3 cm2 V-1 s-1, respectively. Moreover, OFETs based on the two polymers showed good air-stability with negligible changes after being stored under ambient conditions for over 3 months. This journal is
Structure-properties relationships in conjugated molecules based on diketopyrrolopyrrole for organic photovoltaics
Ripaud, Emilie,Demeter, Dora,Rousseau, Théodulf,Boucard-Cétol, Emmanuel,Allain, Magali,Po, Riccardo,Leriche, Philippe,Roncali, Jean
, p. 126 - 133 (2012)
Conjugated systems built by connecting two electron-donor side-chains to a diketopyrrolopyrrole (DPP) core have been synthesized and evaluated as donor material in heterojunction organic solar cells. The effects of composition of the side-chain on the electronic properties of the conjugated system have been analyzed on first series of compounds containing various combinations of benzofuran, benzothiophene, thiophene and furan units. In a second series of compounds, the keto groups of DPP have been replaced by one or two thioketo groups. Results of UV-vis absorption spectroscopy, fluorescence emission spectroscopy and cyclic voltammetry show that the composition of the side-chain has little effect on the HOMO and LUMO levels of the system, but strongly affects the sensitivity of the material toward thermal treatment and thus indirectly the performances of the resulting solar cells. On the other hand, replacement of the keto groups of DPP by thioketo ones leads at the same time to significant reduction of the band gap due to a decrease of the LUMO level, to a quenching of fluorescence and to dramatic decrease of the photovoltaic activity of the molecule.
Synthesis and properties of Zn2+/Cd2+-directed self-assembled metallo-supramolecular polymers based on 1,4-diketo-pyrrolo[3,4-c]pyrrole (DPP) derivatives
Chen, Xuegang,Guo, Kai,Li, Fanchao,Zhou, Li,Qiao, Hongbin
, p. 58027 - 58035 (2014)
New building blocks based on 1,4-diketopyrrolo[3,4-c]pyrrole (DPP), 2,5-bis(2-ethylhexyl)-3,6-bis(5-[p-(2,2':6′,2′′-terpyridine-4′-yl) phenyl]thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (M1) and 2,5-bis(2-ethylhexyl)-3,6-bis(4-[p-(2,2′:6′,2′′-terpyridine-4′-yl) phenyl]phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (M2) were synthesized by the Suzuki Pd-catalyzed cross-coupling reaction. Under moderate conditions, directed self-assembly polymerizations by the transition metal ions Zn2+ and Cd2+, respectively, were carried out. The metallo-supramolecular polymers P1Zn, P1Cd, P2Zn and P2Cd were obtained and fully characterized. The supramolecular polymers P2Zn and P2Cd, containing DPP modified by a phenyl unit, showed absorption maxima at about 504 and 506 nm in films. In contrast, the polymers P1Zn and P1Cd, in which the thiophene moiety-modified DPP was introduced, exhibited strong and broad visible absorption over 300-800 nm with maxima at about 601 and 598 nm and shoulder peaks at about 665 and 671 nm, respectively. The low band gaps estimated from CV of 1.52, 1.51, 1.58 and 1.58 eV for P1Zn, P1Cd, P2Zn and P2Cd, respectively, are also reported.
Multichromophore Donor Materials Derived from Diketopyrrolopyrrole and Phenoxazine: Design, Synthesis, and Photovoltaic Performance
Narayanaswamy, Kamatham,Yadagiri, Bommaramoni,Bagui, Anirban,Gupta, Vinay,Singh, Surya Prakash
, p. 4896 - 4904 (2017)
Herein two conjugated donor molecules, TDPP-POCN and FDPP-POCN, with planar diketopyrrolopyrrole (DPP) as the core building-block acceptor unit and phenoxazine-capped acrylonitriles as arms are designed and synthesized. Solution-processed bulk-heterojunction organic solar cells based on blends of the small-molecule donors and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) exhibit promising photovoltaic device performance with a maximum power conversion efficiency up to 4.8 % for TDPP-POCN and 3.4 % for FDPP-POCN under the illumination of AM1.5G, 100 mW cm–2. To the best of our knowledge, this is the highest efficiency reported so far in DPP–phenoxazine-based systems and among acrylonitrile-bridged donor-π-acceptor-π-donor-structured small-molecule donors for solution-processed small-molecule-based organic solar cells.
Narrow band-gap donor-acceptor copolymers based on diketopyrrolopyrrole and diphenylethene: Synthesis, characterization and application in field effect transistor
Zhu, Haoyun,Huang, Wei,Huang, Yuli,Yang, Junwei,Wang, Weizhi
, p. 37 - 44 (2016)
Three low band-gap diketopyrrolopyrrole based polymers with varying donor groups of furan, thiophene and phenyl were synthesized and then copolymerized with diphenylethene. We investigate the influence of different donor groups and comonomers on the band-gap and field effect transistors. The efficient synthesis of the diketopyrrolopyrrole based copolymers was clearly characterized by a variety of measurements. Two dimensional Grazing Incident X-ray Diffraction was measured to prove that furan and thiophene based copolymers have ordered edge-on structure. These copolymers exhibited strong π-π stacking and excellent hole mobilities when applied in the electric double layer field effect transistors. The high mobility of 2.36 cm2 V-1 s-1 with an on/off ratio of 103 was achieved.
Synthesis and optical properties of photovoltaic materials based on the ambipolar dithienonaphthothiadiazole unit
Nakanishi, Tatsuaki,Shirai, Yasuhiro,Han, Liyuan
, p. 4229 - 4238 (2015)
Dithieno[3′2′:5,6;2′′,3′′:7,8]naphtho[2,3-c][1,2,5]thiadiazole (DTNT) was designed to control the band energies of the polymers for photovoltaic materials. Electrochemical analysis showed that DTNT acts as both an electron donor and an electron acceptor, revealing the ambipolar nature of the DTNT unit. The direct arylation polymerization of DTNT with 2,2′-bithiophene (BTh) and 3,6-bis(2-thienyl)pyrrolo[3,4-c]pyrrole-1,4-dione (DPP) afforded four polymers that differed in either the unit of copolymerization or the chosen side chains. In the PDTNT-BTh series, a shoulder absorption band was observed at a longer wavelength than the intense absorption band. The PDTNT-DPP series exhibited a narrow band gap of less than 1.4 eV and a low HOMO energy of -5.43 eV. An organic photovoltaic cell that contained a PDTNT-BTh polymer with 2-ethylhexyl groups and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM) as an active layer afforded the best performance among the studied compounds, with a JSC of 6.98 mA cm-3, a VOC of 0.758 V, a FF of 0.52, and a PCE of 2.76%.
1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions
Punzi, Angela,Maiorano, Eliana,Nicoletta, Francesca,Blasi, Davide,Ardizzone, Antonio,Ventosa, Nora,Ratera, Imma,Veciana, Jaume,Farinola, Gianluca Maria
, p. 2617 - 2627 (2016)
1,2,3-Triazole rings bearing hydrophobic aliphatic or hydrophilic oligoether chains were easily introduced at the two ends of the conjugated skeleton of bisthiophene-diketopyrrolopyrrole (TDPP) derivatives by simple click cycloaddition reactions. The combination of side chains with different structures and polarities on the triazole rings with the side chains on the N-atoms of the lactam groups of the TDPP moiety enabled the solubility and the solid-state spectroscopic properties of the resulting conjugated molecules to be tuned. Formation of nanostructured aggregates and dependence of their spectroscopic behavior on the substitution pattern were investigated.
Synthesis and Characterization of Diketopyrrolopyrrole-based D-π-A-π-D Small Molecules for Organic Solar Cell Applications
Sivakumar, Gangala,Sasikumar, Mayarambakam,Rao, Vaidya Jayathirtha
, p. 1983 - 1994 (2017)
Four new small molecules – CTDP, BCTDP, CFDP, and BCFDP having D-π-A-π-D molecular architecture, possessing carbazole and benzocarbazole as electron donors, diketopyrrolopyrrole core as acceptor and thiophene/furan acting as spacer/bridge between donor (carbazole and benzocarbazole) and acceptor (diketopyrrolopyrrole) units are synthesized. All the four compounds exhibited absorption in the range of 300 to 700 nm, and, in particular, more intense absorption found in the 500 to 660 nm region. The estimated band gaps are found to be 1.92 eV for CTDP, 1.92 eV for BCTDP, 1.94 eV for CFDP, and 1.92 eV for BCFDP from their intersection point of absorption and emission spectra. The electrochemical studies revealed that the highest occupied molecular orbital/lowest unoccupied molecular orbital energy levels of all the four compounds, CTDP (?5.03/?3.65 eV), BCTDP (?5.03/?3.65 eV), CFDP (?4.94/?3.65 eV), and BCFDP (?4.90/?3.62 eV) are well matched with PCBM and expected to be act as donor materials in small molecule bulk hetero junction organic solar cells. All the compounds are thermally stable up to 382–416°C.
