Synthetic strategies were developed for the preparation of indolo‐imine boron difluoride (IIBD) dyes based on indolo[3,2‐b]carbazole structures. Four new IIBD dyes were synthesized and were subsequently converted into the corresponding ‐BPh2/‐BOR2 and N‐t‐Boc/N‐benzoyl derivatives. The photophysical properties of all dyes were determined in both solution and solid media. All dyes absorb in the UV/Vis region, show negative solvatochromism, and are fluorescent in both media. The absorbance and fluorescence properties of the dyes can be tuned over a wide range by synthetic modifications. These findings are rationalized by theoretical calculations that correspond well to the experimental shifts, explain the negative solvatochromism, and allow quantification of charge transfer (CT). Similarly, the HOMO–LUMO energies measured by CV are in good agreement with the theoretically calculated values. Interestingly, the energy gaps of the dyes can also be tuned by structural modulations using the developed chemical route. Charge transport properties of the dyes were checked and showed that the N‐benzoyl derivative has the highest hole mobility which is useful for organic field effect transistor (OFET) applications. In addition, easy cellular uptake of the dyes, their low toxicity and high stability inside the cells associated with bright fluorescence in the cytoplasm will be useful for their future application as cellular imaging agents. All of these aspects highlight the interest of this new class of dyes.
Organic photovoltaic cells (OPVCs) attract high interest for solar energy harvesting. They are based on organic thin films sandwiched between two electrodes, one of them being transparent and conductive. Nowadays, ITO remains the most widely used transparent conductive electrode (TCE) because of its excellent optical and electrical properties compared to other TCEs. However, it has some drawbacks such as scarcity of indium, high fabrication cost, and mechanical properties poorly adapted to use as flexible substrates. To keep these performances without indium, several materials can replace ITO such as MoO3, ZnO, ZnS, TiO2,… as dielectric and Ag, Cu,... as metal inside a dielectric/metal/dielectric three-layer structure. A Transfer Matrix Method (TMM) based numerical model is used to predict the optical behavior of the considered electrodes. ZnS/Ag/TiOx electrodes are manufactured by a vacuum electron beam evaporator on glass substrates, then characterized by UV-Visible spectrophotometer for obtaining transmittance and reflectance and by a four-point method for the measurement of sheet resistance. It is found that the simulation and experimental curves are quite similar. The transmittance is measured to be higher than 80% on a wide spectral band that can be tailored by the thickness of the upper dielectric material. The optical window Δλ, for T > 80%, can be tuned in the 400–800 nm spectral band, according to the thickness of TiOx in the 25–50 nm range. This variation allows us to adapt our electrode to organic materials in order to optimize the performance of organic solar cells. The sheet resistance obtained is around to 7 Ω/sq, which gives our electrodes the transparent and conductive character simultaneously. A typical parameter to compare the electrodes is the merit figure, which questions the average optical transmission T
av in the visible range and the sheet resistance R
sq. By applying this figure to many manufactured electrodes, the obtained optimal structure of our TCEs is demonstrated to be ZnS (40 nm)/Ag (10 nm)/TiOx (30 nm).
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