92396-89-9Relevant articles and documents
Bis(trialkylsilyl oxide) Silicon Phthalocyanines: Understanding the Role of Solubility in Device Performance as Ternary Additives in Organic Photovoltaics
Brusso, Jaclyn L.,Grant, Trevor M.,Lessard, Beno?t H.,Vebber, Mário C.
, p. 2612 - 2621 (2020)
The use of ternary additives in organic photovoltaics is a promising route for improving overall device performance. Silicon phthalocyanines (SiPcs) are ideal candidates due to their absorption profile, low cost, and ease of synthesis and chemical tunability. However, to date, only a few examples have been reported and specific strategies for aiding in the design of improved ternary additives have not been established. In this study, we report a relationship between ternary additive solubility and device performance, demonstrating that device performance is maximized when the SiPc additive solubility is similar to that of the donor polymer (P3HT, in this case). This improved performance can be attributed to the favored interfacial precipitation of the SiPc when its solubility matches that of the other components of the thin film. The power conversion efficiency (PCE) varied from 2.4% to 3.4% by using axially substituted SiPcs with different solubilities, where the best ternary additive led to a 25% increase in PCE compared to that of the baseline device.
Exploration of silicon phthalocyanines as viable photocatalysts for organic transformations
Dickerson, Shelby D.,Ayare, Pooja J.,Vannucci, Aaron K.,Wiskur, Sheryl L.
, (2021/10/01)
Silicon phthalocyanines have been largely ignored as photocatalysts, despite their low energy excitation, long triplet lifetimes, and their ability to form singlet oxygen. By incorporating alkyl and silicon protecting groups as axial ligands on the silico
Bis(tri-n-alkylsilyl oxide) silicon phthalocyanines: A start to establishing a structure property relationship as both ternary additives and non-fullerene electron acceptors in bulk heterojunction organic photovoltaic devices
Dang, Minh-Trung,Grant, Trevor M.,Yan, Han,Seferos, Dwight S.,Lessard, Beno?t H.,Bender, Timothy P.
, p. 12168 - 12182 (2017/07/10)
Previous studies have shown that the use of bis(tri-n-hexylsilyl oxide) silicon phthalocyanine ((3HS)2-SiPc) as a solid ternary electroactive additive in poly(3-hexylthiophene):phenyl-C61-butyric acid methyl ester P3HT:PC61BM bulk heterojunction organic photovoltaic (BHJ OPV) devices resulted in an increased performance. It has been hypothesized that the increase in efficiency is partially due to the unique and odd combination of high solubility and strong driving force of crystallization previously observed for (3HS)2-SiPc. In this follow-up study, two chemical variants of (3HS)2-SiPc, namely bis(tri-n-butylsilyl oxide) ((3BS)2-SiPc) and bis(tri-n-isopropylsilyl oxide) ((3TS)2-SiPc) were synthesized to determine how small changes in the chemical structure would affect the properties of the material and its performance within BHJ OPV devices. We observed that the use of either (3XS)2-SiPc compound results in a further ～10% increase in JSC compared to the use of (3HS)2-SiPc. We also did a preliminary assessment of the use of three (3XS)2-SiPcs as replacements for PC61BM in straight binary P3HT-based BHJ OPV devices. Despite achieving only ～1% PCE efficiencies, observations including a ≈50% increase in VOC over a P3HT:PC61BM baseline and a decent fill factor indicate to us that (3XS)2-SiPcs do have potential as non-fullerene acceptors and advantageous alternatives due to their low embedded energy and therefore their inherent sustainability. X-ray diffraction of ternary and binary BHJ devices demonstrates that both (3BS)2-SiPc and (3TS)2-SiPc experienced similar increase in crystallite density (d-spacing) relative to (3HS)2-SiPc which we surmise plays a role in the improved device efficiency. Like (3HS)2-SiPc, for these two new additives, we also observed a high tendency of crystallization. The results from this study suggest that solubility and driving force to crystallize are important factors in determining the extent to which an additive will migrate to the donor/acceptor interface and thus affect its performance as a ternary additive in BHJ OPV devices. Based on the three (3XS)2-SiPcs used in this study, the smaller tri-n-alkylsilyl oxide molecular fragments seem to work better. Therefore, moving forward, we will continue to consider smaller molecular fragments that still enable solubility and processability of (3XS)2-SiPcs.
PREPARATION OF SILICON PHTHALOCYANINES AND GERMANIUM PHTHALOCYANINES AND RELATED SUBSTANCES
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Page/Page column 10-11, (2010/05/13)
A process for preparing compounds of the general formula (I) by reacting the compound of the general formula (II) where L, L′ are the same or different and are each independently Cl or OH in the presence of a. chlorine compounds Cl-M2R1R2R3, Cl-M3R4R5R6, with the proviso that L and L′ are not both simultaneously OH, or b. hydroxyl compounds HO-M2R1R2R3, HO-M3R4R5R6. The use of compounds of the general formula (I) as markers for liquids and a process for detecting markers in liquids.
