- Synthesis and Spectroscopic Investigation of Diketopyrrolopyrrole - Spiropyran Dyad for Fluorescent Switch Application
-
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.
- Doddi, Siva,Narayanaswamy,Ramakrishna, Bheerappagari,Singh, Surya Prakash,Bangal, Prakriti Ranjan
-
-
Read Online
- Synthesis and characterization of a narrow-bandgap polymer containing alternating cyclopentadithiophene and diketo-pyrrolo-pyrrole units for solar cell applications
-
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%.
- Chen, Guan-Yu,Chiang, Chien-Ming,Kekuda, Dhananjay,Lan, Shang-Che,Chu, Chih-Wei,Wei, Kung-Hwa
-
-
Read Online
- Air-stable ambipolar organic field-effect transistors based on naphthalenediimide-diketopyrrolopyrrole copolymers
-
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
- Wang, Ping,Li, Hui,Gu, Chunling,Dong, Huanli,Xu, Zhenzhen,Fu, Hongbing
-
-
Read Online
- Structure-properties relationships in conjugated molecules based on diketopyrrolopyrrole for organic photovoltaics
-
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.
- Ripaud, Emilie,Demeter, Dora,Rousseau, Théodulf,Boucard-Cétol, Emmanuel,Allain, Magali,Po, Riccardo,Leriche, Philippe,Roncali, Jean
-
-
Read Online
- Synthesis and properties of Zn2+/Cd2+-directed self-assembled metallo-supramolecular polymers based on 1,4-diketo-pyrrolo[3,4-c]pyrrole (DPP) derivatives
-
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.
- Chen, Xuegang,Guo, Kai,Li, Fanchao,Zhou, Li,Qiao, Hongbin
-
-
Read Online
- Multichromophore Donor Materials Derived from Diketopyrrolopyrrole and Phenoxazine: Design, Synthesis, and Photovoltaic Performance
-
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.
- Narayanaswamy, Kamatham,Yadagiri, Bommaramoni,Bagui, Anirban,Gupta, Vinay,Singh, Surya Prakash
-
-
Read Online
- Narrow band-gap donor-acceptor copolymers based on diketopyrrolopyrrole and diphenylethene: Synthesis, characterization and application in field effect transistor
-
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.
- Zhu, Haoyun,Huang, Wei,Huang, Yuli,Yang, Junwei,Wang, Weizhi
-
-
Read Online
- Synthesis and optical properties of photovoltaic materials based on the ambipolar dithienonaphthothiadiazole unit
-
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%.
- Nakanishi, Tatsuaki,Shirai, Yasuhiro,Han, Liyuan
-
-
Read Online
- 1,2,3-Triazole-Diketopyrrolopyrrole Derivatives with Tunable Solubility and Intermolecular Interactions
-
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.
- Punzi, Angela,Maiorano, Eliana,Nicoletta, Francesca,Blasi, Davide,Ardizzone, Antonio,Ventosa, Nora,Ratera, Imma,Veciana, Jaume,Farinola, Gianluca Maria
-
-
Read Online
- Synthesis and Characterization of Diketopyrrolopyrrole-based D-π-A-π-D Small Molecules for Organic Solar Cell Applications
-
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.
- Sivakumar, Gangala,Sasikumar, Mayarambakam,Rao, Vaidya Jayathirtha
-
-
Read Online
- Charge separation and singlet fission in covalently linked diketopyrrolopyrrole derivatives and triphenylamine triad in solution
-
A covalently linked push-pull type triad containing two unsymmetrical electron donors, triphenylamine (TPA) and benzothiophene (BT), and diketopyrrolopyrrole (DPP), an electron acceptor, through thiophene spacer has been synthesized (BT-DPP-TPA(7)) and ultrafast relaxation dynamics of the triad has been explored in solution phase by various spectroscopic methods. Steady-state and time-resolved emission studies show the efficient fluorescence quenching of the DPP entity of as prepared BT-DPP-TPA(7) triad. The negative free energy values comprising the redox potentials and singlet state energy of BT-DPP-TPA(7) revealed the probability of electron transfer from the singlet ground state of TPA to the excited singlet state of DPP. Femtosecond transient absorption (fsTA) spectroscopic studies confirmed the formation of charge separation state by detecting triphenylamine radical cation as electron-transfer transients. The rate of charge separation, kCS, is (109?108 s?1) observed to be increasing from nonpolar to polar solvents and the rate of charge recombination, kCR, was found to be slower (μs time scale) in polar solvents like DMF and chloroform, than that in hexane, non-polar solvent (ns time scale). This novel aspect could be due to asymmetrically designed push-pull type triad, a feature that was not evident in push-pull triad constructed using symmetric TPA as electron donors. Furthermore, fsTA studies also demonstrate, for the first time, that the DPP derivatives, TDPP(4) and BT-DPP-TPA(7), both undergo singlet fission (SF) event (S→TT) in 100?200 ps time scale in solution phase for the solution of concentration above ～100 μM. These results may pave the new avenue for device design comprising DPP derivatives.
- Bangal, Prakriti Ranjan,Chakali, Madhu,Dyaga, Bharath,Mandal, Haraprasad,Rao, V. Jayathirtha,Venkatesan, Munisamy
-
-
Read Online
- Synthesis, characterization and photovoltaic properties of platinum-containing poly(aryleneethynylene)polymers with electron-deficient diketopyrrolopyrrole unit
-
Three new solution-processable Pt(II)-containing poly(aryleneethynylene)polymers based on diketopyrrolopyrrole moiety and their corresponding diplatinum model complexes were synthesized via the Sonogashira-type coupling reaction of the platinum(II)chloride precursor and each of the diethynyl ligands. The photophysical, thermal stability, electrochemical, carrier mobility and photovoltaic properties of these polymers were fully investigated. These polymers exhibit strong absorption bands in the range of 550–750 nm, and fluorescent bands between 650 and 850 nm. One thiophene flanked diketopyrrolopyrrole based polymer with linear n-octyl chains shows a better photovoltaic performance than that made from the branched 2-ethylhexyl analogue.
- Zhan, Hongmei,Liu, Qian,So, Shu-Kong,Wong, Wai-Yeung
-
-
Read Online
- Incorporation of furan into low band-gap polymers for efficient solar cells
-
The design, synthesis, and characterization of the first examples of furan-containing low band-gap polymers, PDPP2FT and PDPP3F, with substantial power conversion efficiencies in organic solar cells are reported. Inserting furan moieties in the backbone of the conjugated polymers enables the use of relatively small solubilizing side chains because of the significant contribution of the furan rings to overall polymer solubility in common organic solvents. Bulk heterojunction solar cells fabricated from furan-containing polymers and PC71BM as the acceptor showed power conversion efficiencies reaching 5.0%.
- Woo, Claire H.,Beaujuge, Pierre M.,Holcombe, Thomas W.,Lee, Olivia P.,Frechet, Jean M. J.
-
-
Read Online
- Alternating copolymers of diketopyrrolopyrrole or benzothiadiazole and alkoxy-substituted oligothiophenes: Spectroscopic, electrochemical and spectroelectrochemical investigations
-
A series of solution processable semiconducting donor-acceptor (DA) copolymers consisting of either diketopyrrolopyrrole or benzothiadiazole A units and alkoxy- or alkyl-substituted oligothiophene D units were synthesized. For all prepared copolymers the measured XPS spectra (C1s, S2p, N1s and O1s) were in a very good agreement with the expected chemical constitution. Spectroscopic studies of the synthesized copolymers showed that their optical band gaps were governed by the presence of the alkoxy substituents whose electron donating properties led to additional gap narrowing yielding semiconductors with band gaps of below 1.3 eV in the case of the polymers with the diketopyrrolopyrrole A unit. The same trend was observed with the electrochemical band gaps, whose values were however found to be ca. 0.4 eV superior to the corresponding optical band gaps values. Vibrational model was calculated for two of the synthesized copolymers with the goal to unequivocally attribute the observed Raman modes and to support the interpretation of the spectral changes induced by the electrochemical oxidation. It was established that the electrochemical oxidative doping of the copolymer with the benzothiadiazole A unit is limited to the oligothiophene segment in which the charge of the formed polycation is localized. To the contrary, in the case of the polymer with the diketopyrrolopyrrole A segment the charge imposed on the oligothiophene segment delocalizes towards the diketopyrrolopyrrole unit. These findings are in perfect agreement with the UV-vis-NIR spectroelectrochemistry data which show strong localization of electrochemically created charge carriers in the benzothiadiazole - oligothiophene copolymer and their metallic-like delocalization in the diketopyrrolopyrrole one. The latter seems to be very interesting not only as a potential low band gap component of organic photovoltaic cells but also, in the doped state, as electronic conductor of metallic character.
- Gora,Krzywiec,Mieczkowski,Rodrigues Maia,Louarn,Zagorska,Pron
-
-
Read Online
- Hetero aromatic donors as effective terminal groups for DPP based organic solar cells
-
Four new solution-processable donor-acceptor-donor (D-A-D) structured low bandgap small molecules (CSDPP5, CSDPP6, CSDPP7 and CSDPP8) with diketopyrrolopyrrole as central acceptor unit and phenoxazine (POZ) or carbazole (CBZ) as terminal units were designed, synthesized and characterized. The new small molecules have been employed as donors along with the PC71BM as electron acceptor in solution processed BHJ organic solar cells, showed broad absorption bands with suitable electrochemical energy levels. When the BHJ active layer was cast from THF solvent, the optimal power conversion efficiencies obtained with CSDPP5, CSDPP6, CSDPP7 and CSDPP8 are 2.97% 3.06%, 2.42% and 2.43% respectively. The PCE of the devices when processed with DIO/THF solvent, have been further enhanced to 4.69%, 4.14% for CSDPP6:PC71BM and CSDPP8:PC71BM active layers respectively. The enhancement in PCE has been attributed to change in nanoscale morphology and more balanced charge transport resulting from increased hole mobility.
- Reddy, Marri Anil,Kumar, Ch. Pavan,Ashok, Akudari,Sharma, Abhishek,Sharma,Chandrasekharam, Malapaka
-
-
Read Online
- Panchromatic Push-Pull Dyes of Elongated Form from Triphenylamine, Diketopyrrolopyrrole, and Tetracyanobutadiene Modules
-
Several symmetrical and unsymmetrical thiophene-functionalized diketopyrrolopyrrole chromophores bearing a bis(p-methoxyphenyl)-p-phenylamine substituent were synthesized through palladium-catalyzed cross-coupling reactions. Mono-substitution and di-substitution occur using either alkyne or borolane groups, allowing the preparation of mixed systems. The alkyne derivatives could be prepared in high yields, and are versatile building blocks for the [2+2] cyAcloaddition of tetracyanoethylene, leading to 1,1,4,4-tetracyanobuta-1,3-diene derivatives. These interesting push-pull molecules exhibit a rich redox activity, which is understandable in light of the behavior of appropriate reference compounds. These innovative and rationally designed scaffolds are highly colored, exhibiting high absorption coefficients and spanning an absorption range of more than 600A nm of the UV/Vis electromagnetic spectrum.
- Heyer, Elodie,Ziessel, Raymond
-
-
Read Online
- Use of side-chain for rational design of n-type diketopyrrolopyrrole-based conjugated polymers: What did we find out?
-
The primary role of substituted side chains in organic semiconductors is to increase their solubility in common organic solvents. In the recent past, many literature reports have suggested that the side chains play a critical role in molecular packing and strongly impact the charge transport properties of conjugated polymers. In this work, we have investigated the influence of side-chains on the charge transport behavior of a novel class of diketopyrrolopyrrole (DPP) based alternating copolymers. To investigate the role of side-chains, we prepared four diketopyrrolopyrrole-diketopyrrolopyrrole (DPP-DPP) conjugated polymers with varied side-chains and carried out a systematic study of thin film microstructure and charge transport properties in polymer thin-film transistors (PTFTs). Combining results obtained from grazing incidence X-ray diffraction (GIXD) and charge transport properties in PTFTs, we conclude side-chains have a strong influence on molecular packing, thin film microstructure, and the charge carrier mobility of DPP-DPP copolymers. However, the influence of side-chains on optical properties was moderate. The preferential "edge-on" packing and dominant n-channel behavior with exceptionally high field-effect electron mobility values of >1 cm2 V-1 s-1 were observed by incorporating hydrophilic (triethylene glycol) and hydrophobic side-chains of alternate DPP units. In contrast, moderate electron and hole mobilities were observed by incorporation of branched hydrophobic side-chains. This work clearly demonstrates that the subtle balance between hydrophobicity and hydrophilicity induced by side-chains is a powerful strategy to alter the molecular packing and improve the ambipolar charge transport properties in DPP-DPP based conjugated polymers. Theoretical analysis supports the conclusion that the side-chains influence polymer properties through morphology changes, as there is no effect on the electronic properties in the gas phase. The exceptional electron mobility is at least partially a result of the strong intramolecular conjugation of the donor and acceptor as evidenced by the unusually wide conduction band of the polymer. the Partner Organisations 2014.
- Kanimozhi, Catherine,Yaacobi-Gross, Nir,Burnett, Edmund K.,Briseno, Alejandro L.,Anthopoulos, Thomas D.,Salzner, Ulrike,Patil, Satish
-
-
Read Online
- Mono-/Bimetallic Neutral Iridium(III) Complexes Bearing Diketopyrrolopyrrole-Substituted N-Heterocyclic Carbene Ligands: Synthesis and Photophysics
-
The synthesis and photophysics (UV-vis absorption, emission, and transient absorption) of four neutral heteroleptic cyclometalated iridium(III) complexes (Ir-1-Ir-4) incorporating thiophene/selenophene-diketopyrrolopyrrole (DPP)-substituted N-heterocyclic carbene (NHC) ancillary ligands are reported. The effects of thiophene versus selenophene substitution on DPP and bis- versus monoiridium(III) complexation on the photophysics of these complexes were systematically investigated via spectroscopic techniques and density functional theory calculations. All complexes exhibited strong vibronically resolved absorption in the regions of 500-700 nm and fluorescence at 600-770 nm, and both are predominantly originated from the DPP-NHC ligand. Complexation induced a pronounced red shift of this low-energy absorption band and the fluorescence band with respect to their corresponding ligands due to the improved planarity and extended π-conjugation in the DPP-NHC ligand. Replacing the thiophene units by selenophenes and/or biscomplexation led to the red-shifted absorption and fluorescence spectra, accompanied by the reduced fluorescence lifetime and quantum yield and enhanced population of the triplet excited states, as reflected by the stronger triplet excited-state absorption and singlet oxygen generation.
- Hobbie, Erik K.,Kilina, Svetlana V.,Lystrom, Levi,Pan, Yanxiong,Sun, Wenfang,Sun, Xinyang,Thomas, Salim A.,Wang, Hua,Xu, Wan,Yang, Zhongyu
-
p. 15278 - 15290
(2021/10/20)
-
- Diketopyrrolopyrrole derivative and application thereof
-
The invention provides a diketopyrrolopyrrole derivative and application thereof as well as relates to a diketopyrrolopyrrole derivative. The structural formula of the diketopyrrolopyrrole derivativeis as shown in a formula (I): the formula (I) is as shown in the description; in the formula (I), R1 is selected from a group as shown in a formula (I-a), a formula (I-b), a formula (I-c), a formula (I-d) or a formula (I-e) (the formulas are as shown in the description); and in the formula (I-a), the formula (I-b), the formula (I-c), the formula (I-d) and the formula (I-e), * shows connection position. The diketopyrrolopyrrole derivative has excellent photoelectric property and can be applied in the field of organic photoelectric functional devices.
- -
-
-
- Substituent-eliminable diketopyrrolopyrrole derivative, organic semiconductor material precursor solution, organic semiconductor material, and organic semiconductor material film
-
A substituent-eliminable diketopyrrolopyrrole derivative represented by the following formula (I) is provided. In the formula (I), R represents a substituted or unsubstituted alkyl group; X represents a substituted or unsubstituted alkyl group; Ar represents a substituted or unsubstituted aromatic group or a substituted or unsubstituted heteroaromatic group; and n represents an integer of from 1 to 4.
- -
-
-
- NOVEL COMPOUND AND PHOTOELECTRIC CONVERSION DEVICE HAVING THE SAME
-
The present specification of the photoelectric conversion element is the life, efficiency, electrochemical stability and thermal stability can be compound, said compound number. under public affairs including photoelectric conversion element. Specifically photoelectric conversion region of. under public affairs number organic solar cell. (by machine translation)
- -
-
-
- B thienyl pyrrolo pyrrole dione-naphthyl conjugated derivative and its preparation method and application
-
The invention discloses a preparation method of a bithienyl pyrrolopyrroledione-naphthyl conjugated derivative and an application of the derivative as a small molecule electronic donor material in a photoelectric conversion active layer in organic bulk heterojunction solar batteries. Due to coupling of bithienyl pyrrolopyrroledione and a naphthyl derivative, the prepared material has good visible-near infrared light absorption property and high hole mobility, solubility and photoelectric conversion efficiency. According to the preparation method of the derivative, a target product is obtained through reaction of Suzuki coupling and the like. The derivative is simple in synthesis method, explicit in structure and easy to purify, high photoelectric conversion property is realized in simple molecules, and the derivative has the potential application prospect in the aspect of application in low-cost organic solar batteries.
- -
-
-
- Solvatochromism in diketopyrrolopyrrole derivatives: Experimental and computational studies
-
A series of seven thiophen-substituted diketopyrrolopyrrole derivatives were synthesised and their solution absorption spectra characterised in a range of solvents of varying polarity. The absorption spectra of these diketopyrrolopyrrole derivatives exhibited significant negative solvatochromism. The behaviour is consistent with results of time-dependent density-functional theory calculations of excitation energies. Calculated electronic structures suggest that there is significant charge transfer between the electron-donating thiophen substituents and the diketopyrrolopyrrole core but that the magnitude of this charge shift is reduced in the excited state compared with the ground state. The resulting reduction in polarity of the excited state accounts for the negative solvatochromism observed. The implications of the results for the potential application of diketopyrrolopyrrole compounds as photovoltaic materials are considered.
- Szabadai, Rebecca S.,Roth-Barton, Jesse,Ghiggino, Kenneth P.,White, Jonathan M.,Wilson, David J. D.
-
p. 1330 - 1337
(2014/11/08)
-
- Synthesis and electrochemical properties of porphycene-diketopyrrolopyrrole conjugates
-
The selective iodination of 2,7,12,17-tetrahexylporphycene 1 was successfully accomplished by using N-iodosuccinimide in the presence of activators to give 3-iodoporphycene 2 and 3,13-diiodoporphycene 3a. These iodinated porphycenes can be used as the substrates for palladium-catalyzed coupling to prepare porphycene-diketopyrrolopyrrole conjugates in two steps. The connection of the diketopyrrolopyrrole units to porphycenes broadened their absorption spectra and increased the intensity of the Q-bands due to the electronic interactions between the porphycene and diketopyrrolopyrrole moieties.
- Okabe, Takuya,Kuzuhara, Daiki,Suzuki, Mitsuharu,Aratani, Naoki,Yamada, Hiroko
-
supporting information
p. 3508 - 3511
(2014/07/21)
-
- Self-organizing mesomorphic diketopyrrolopyrrole derivatives for efficient solution-processed organic solar cells
-
We describe the synthesis, self-organization, and photovoltaic properties of diketopyrrolopyrrole (DPP)-based mesomorphic small-molecule materials, 3,6-bis{5-(4-alkylphenyl)thiophen-2-yl}-2,5-di(2-ethylhexyl)-pyrrolo[3,4-c] pyrrole-1,4-diones (DPP-TP6 and DPP-TP12), which have strong visible absorption characteristics. The effects of varying terminal alkyl chains on the self-assembling properties and photovoltaic device performances have been studied. With the appropriate ratio of the lengths of the alkyl chains to its rigid DPP core, DPP-TP6 exhibits liquid-crystalline properties and forms well-developed nanostructured bulk heterojunction (BHJ) architectures with a fullerene derivative (PC71BM). Organic solar cells (OSCs) employing BHJ DPP-TP6:PC71BM films show a power conversion efficiency as high as 4.3% with a high open-circuit voltage of 0.93 V and a fill factor of 0.55. These results demonstrate that liquid-crystalline organization to direct molecular self-assembly is a promising strategy for fabricating high-performance solution-processed small-molecule OSCs.
- Shin, Woong,Yasuda, Takuma,Watanabe, Go,Yang, Yu Seok,Adachi, Chihaya
-
p. 2549 - 2556
(2013/07/26)
-
- C-H activation: Making diketopyrrolopyrrole derivatives easily accessible
-
Diketopyrrolopyrrole (DPP) derivatives are an important class of high-performance pigment used in inks, paints, plastics, and organic electronics. Until now, DPP derivatives containing sophisticated aryl units at the DPP core have usually been obtained via Suzuki, Stille, or Negishi cross-coupling reactions, which require organometallic precursors. In this work, a series of DPP-based π-conjugated molecules bearing diverse aryl substituents on the thiophene- or benzene-DPPs were facilely synthesized in moderate to excellent yields through the Pd-catalyzed direct arylation of C-H bonds. The synthetic procedures feature advantages over traditional C-C cross-coupling reactions such as: (1) avoidance of the use of organometallic reagents in the starting materials leading to simpler byproducts and higher atom economy, (2) fewer synthetic steps, (3) higher yields, (4) better compatibility with chemically sensitive functional groups, and (5) simpler catalytic systems free of phosphine ligands. These advantages make the present protocol an ideal and versatile strategy for the synthesis of DPP derivatives, especially for structurally complicated DPPs that may possess chemically sensitive functionalities. The optical and electrochemical properties of the synthesized DPPs (17 compounds) were systematically investigated using UV-vis spectroscopy, steady-state fluorescence spectroscopy, and cyclic voltammetry (CV).
- Liu, Shi-Yong,Shi, Min-Min,Huang, Jia-Chi,Jin, Zheng-Neng,Hu, Xiao-Lian,Pan, Jun-Ying,Li, Han-Ying,Jen, Alex K.-Y.,Chen, Hong-Zheng
-
p. 2795 - 2805
(2013/07/31)
-
- Metal-free and fluorescent diketopyrrolopyrrole fluorophores for dye-sensitized solar cells
-
Novel metal-free and fluorescent dipyrrolopyrrole (DPP) dyes consisting of a central bis(lactam)-bearing pendent benzyl or branched hydrocarbon groups as solubilizing fragments and two orthogonal side arms (dimethylaminopropyne and benzoate anion) have been designed and synthesized. The UV/Vis absorption spectra recorded in THF are dominated by intense low-energy π-π absorptions centered at 488 nm or 602 nm, respectively, for the phenyl- or thiophene-based DPP dyes. The fluorescence spectra also display broad bands at 555 nm (τF= 0.57 and ΦF=4.6 ns) for the phenyl- and at 624 nm (ΦF=0.31 and ΦF=3.5 ns) for the thiophene-based molecular structures. Under standard global AM 1.5G irradiation a maximum photon-to-electron conversion efficiency of 2.54% was achieved with dye-sensitized solar cells based on nanocrystalline TiO2 (Jsc=7.5 mAcm-2, Voc=0.49 V, and FF=0.70) for the phenyl-based DPP dye and 1.89% (Jsc=7.1 mAcm-2, Voc= 0.41 V, and FF=0.65) for the thiophene-based DPP dye.
- Hablot, Delphine,Islam, Ashraful,Han, Liyuan,Ziessel, Raymond
-
p. 462 - 469
(2014/01/17)
-
- PYRROLOPYRROLE DERIVATIVES, THEIR MANUFACTURE AND USE
-
The present invention relates to compounds of the formula (I) wherein the substituents are as defined in claim 1, and their use as organic semiconductor in organic devices, like diodes, organic field effect transistors and/or a solar cells. The compounds of the formula I have excellent solubility in organic solvents. High efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when said compounds are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).
- -
-
Page/Page column 33; 34
(2009/05/30)
-
- DIKETOPYRROLOPYRROLE POLYMERS AS ORGANIC SEMICONDUCTORS
-
The present invention relates to polymers comprising a repeating unit of the formula (l) and their use as organic semiconductor in organic devices, especially a diode, an organic field effect transistor and/or a solar cell, or a device containing a diode and/or an organic field effect transistor, and/or a solar cell. The polymers according to the invention have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers according to the invention are used in semiconductor devices or organic photovoltaic (PV) devices (solar cells).
- -
-
Page/Page column 43
(2008/06/13)
-
