Rainbow Perylene Monoimides: Easy Control of Optical Properties (original) (raw)
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New perylene derivative dyes for dye-sensitized solar cells
Solar Energy Materials and Solar Cells, 2007
We have studied the influence of the spacer alkyl chain length of perylenemonoimide (PMI) dyes on the device performance in dye-sensitized solar cells (DSSCs). We observed that the dyes with longer and brunched alkyl chains exhibit higher efficiencies in DSSCs. In line with these statements we now report the highest efficiency obtained under standard conditions for a perylene imide derivative with PMI-DA1 that performs 300 mV open circuit voltage, 9.79 mA/cm2 short-circuit current and 1.61% overall conversion efficiency.
The Journal of Physical Chemistry C, 2007
Solar cell device measurements and fabrication S3 Experimental setup S4 Quantum chemical calculations S5 Synthesis and characterization S1 UV-vis The blue shift upon adsorption of perylenes with an anhydride group on TiO 2 has previously been assigned to the ring-opening (ref 27, 28 in main article) based on UV-vis and the disappearance of the anhydride stretch in IR (ref 28 supporting info). We see the same behaviour in the equivalence between the UV-vis spectra for the anhydride open form (the salts) and the spectra for the dyes on TiO 2. The ring-closed dyes were treated with Na 2 CO 3 in THF solution, forming the disodium salts and was compared with the spectra of the dyes on TiO 2 , showing an almost identical shift for all cases. UV-vis on a directly synthesized ID28 salt (see figure 1 below) was also compared with the spectrum of the ID28 dye on TiO 2 with the same result. We have performed quantum chemical calculations and theoretically quantified this effect and in one case also added the local interaction with TiO 2 (for ID34 in table 6 found in S4 below).
Amphiphilic and chiral unsymmetrical perylene dye for solid-state dye-sensitized solar cells
Turkish Journal of Chemistry
A novel amphiphilic, unsymmetrically substituted N-((2S)-2-aminohexanoic acid)-N-[(S)-1-phenylethyl]-3,4,9,10-perylenetetracarboxydiimide with 2 different chiral centers was synthesized and characterized. Chiral amphiphilicity, which can be tunable between hydrophilic and hydrophobic parts, is responsible for controlled self-assembly through intermolecular hydrogen bonding (N-H • • • O). The product showed high thermal stability but partial solubility in common organic solvents. We observed 2 isosbestic points at 533 and 611 nm, confirming the presence of overlapped monomer and excimer emissions in the temperature range of 10-80 • C. Fluorescence quenching in m-cresol was attributed to charge-transfer interactions. Importantly, the excited state of the chiral dye can decay only by fluorescence in the solid state, mainly due to O-H • • • N hydrogen bonds. Novel red-light-emitting (λem = 658 nm) chiral perylene dye has a great potential for solid-state lighting technologies.
Piperidine-Substituted Perylene Sensitizer for Dye-Sensitized Solar Cells
Advances in OptoElectronics, 2011
We have prepared a novel piperidine-donor-substituted perylene sensitizer,PK0002, and studied the photovoltaic performance in dye-sensitized solar cells (DSSCs). Physical properties and photovoltaic performance of this new perylene derivativePK0002are reported and compared with those of unsubstituted perylene sensitizer,PK0003. PK0002, when anchored to nanocrystalline TiO2films, achieves very efficient sensitization across the whole visible range extending up to 800 nm. The incident photon-to-current conversion efficiency (IPCE) spectrum was consistent with the absorption spectrum and resulted in a high short-circuit photocurrent density (Jsc) of 8.8 mA cm-2.PK0002showed higher IPCE values thanPK0003in the 520–800 nm region. Under standard AM 1.5 irradiation (100 mW cm-2) and using an electrolyte consisting of 0.6 M dimethylpropyl-imidazolium iodide, 0.05 M I2, 0.1 M LiI, and 0.5 Mtert-butylpyridine in acetonitrile, a solar cell containing sensitizerPK0002yielded a short-circuit pho...
Energy & Environmental Science, 2011
Compounds N-(2,5-di-tert-butylphenyl)-perylene-1,6-di(4-tert-butylphenoxy)-9bromo-3,4-dicarboximide (1), 1 benzyl 4-hydroxybenzoate, 2 N-Octylnaphthalene-1,8dicarboxyanhydride-4,5-di-carboximide 3 (4), N-Amino-N′-octylnaphthalene-1,8:4,5tetracarboxydiimide (5) 3 , 1,6-di(4-tert-butylphenoxy)-9-bromo-perylene-3,4dicarboxylicanhydride (8), 3 4-(5,5-dimethyl-1,3-dioxan-2-yl)aniline (9), 4 N-(2,5-di-tertbutylphenyl)-perylene-1,6-di(4-tert-butylphenoxy)-9-(4-carboxyphenoxy)-3,4dicarboximide (19) 5 were prepared according to literature methods.
Three near-infrared (NIR) absorbing unsymmetrical perylene diimide DeAeD type dyes containing 6-undecanoxy as donor group were utilized in dye-sensitized nanocrystalline TiO 2 solar cells. Structure of the acceptor side of the molecules were improved by adding 4-[2-methyl-5-(cyanoacrylic acid)-3thienyl]-phenyl (V), 3-carboxy-2-pyridil (VI) and 3-carboxy-2-pyrazyl (VII) moieties attached to one of the N-side of the dye. The relationship between the molecular structure of the acceptor sites of the dyes and the photovoltaic performances were discussed. Electrochemical measurements indicated that band gaps of the dyes were energetically favorable for electron injection from the excited state of the dyes to the conduction band of TiO 2 nanoparticles. However, three dyes gave lower conversion efficiency on DSSC applications. Strong electron-withdrawing nature of perylene core might not permit to transfer the photo-generated electrons to the carboxyl groups anchoring to TiO 2 surface, and then solar-to-electricity conversion efficiencies of the dyes were reduced.
Journal of Power Sources, 2009
Two new symmetrical compounds A and P based on perylene-anthracene and perylene-pyrene, respectively, were synthesized and characterized by FT-IR, 1 H NMR, TGA and TMA. These compounds contained tert-butyl groups which enhanced their solubility, decomposed above 400 • C and gave char yields of 46-65% at 800 • C in N 2 . Compound A showed significantly higher glass transition temperature (124 • C) than P (75 • C). Their absorption spectra were broad with longer wavelength absorption at 467-525 nm and optical band gap of 2.05 eV. The solutions of the compounds emitted green-yellow light with maximum at 555 nm, while their films were not photoluminescent. The compound A shows better photovoltaic response than compound P. Quasi solid state dye sensitized solar cells (DSSCs) have been fabricated employing compound A as sensitizer and polymer sol gel as electrolyte and characterized through the current-voltage characteristics in dark as well as under illumination and electrochemical impedance spectra. We found that the Al 2 O 3 modification of TiO 2 layer significantly improves the dye absorption resulting in enhancement of power conversion efficiency (PCE) (from 1.15 to 2.13%) which is attributed to the increase in electron lifetime and reduction in back transfer of electrons. Finally, the TiO 2 has been incorporated into the polymer electrolyte gel to improve the power conversion efficiency (3.42%) of the quasi solid state DSSC. The faster electron diffusion in the device, the high ionic conductivity and the low activation energy of the polymer electrolyte are also responsible for enhanced PCE, when TiO 2 nano-particles are incorporated in the polymer electrolyte.
The journal of physical chemistry. A, 2018
This paper reports new D-D-π-A dyes based on N-annulated perylene, emphasizing the enhanced dye-to-semiconductor charge-transfer mechanism. A series of DFT calculations for new tPA-perylene-based dyes was conducted, starting from the systematic selection of DFT methods by reproducing the experimentally obtained properties of known perylene-based sensitizers. Accordingly, using the LC-ωPBE xc functional with 6-31+G(d) basis set for the time-dependent calculations of the excitation energies, a damping parameter of ω = 0.150 Bohr was found to be most appropriate for dyes having spatial orbital overlap value of 0.21 ≤ Λ ≤ 0.38, while ω = 0.175 Bohr is suitable for analogues with 0.43 ≤ Λ ≤ 0.57. Moreover, the mPWHandHPW91/6-31G(d) method gave high accuracy in GSOP calculations. The comparison between the properties of tPA-based donor groups has revealed that the semirigid tPA-based D4 unit is an effective donor group for perylene-based dye. Initial screening of the acceptor designs resu...