273-15-4Relevant articles and documents
Highly Efficient Luminescent Solar Concentrators Based on Benzoheterodiazole Dyes with Large Stokes Shifts
Gao, Sheng,Balan, Bamisha,Yoosaf, Karuvath,Monti, Filippo,Bandini, Elisa,Barbieri, Andrea,Armaroli, Nicola
, p. 11013 - 11023 (2020/06/08)
Five extended π-conjugated systems with electron donor (D) and acceptor (A) moieties have been synthesized. Their basic D-A-D structural motif is a benzothiadiazole unit symmetrically equipped with two thiophene rings (S2T). Its variants include 1) the same molecular framework in which sulfur is replaced by selenium (Se2T), also with four thiophene units (Se4T) and 2) a D’-D-A-D system having a N-carbazole donor moiety at one end (CS2T) and a D’-D-A-D-A’ array with a further acceptor carbonyl unit at the other extremity (CS2TCHO). The goal is taking advantage of the intense luminescence and large Stokes shifts of the five molecules for use in luminescent solar concentrators (LSCs). All of them exhibit intense absorption spectra in the UV/Vis region down to 630 nm, which are fully rationalized by DFT. Emission properties have been studied in CH2Cl2 (298 and 77 K) as well as in PMMA and PDMS matrices, measuring photoluminescence quantum yields (up to 98 percent) and other key optical parameters. The dye–PMMA systems show performances comparable to the present state-of-the-art, in terms of optical and external quantum efficiencies (OQE=47.6 percent and EQE=31.3 percent, respectively) and flux gain (F=10.3), with geometric gain close to 90. LSC devices have been fabricated and tested in which the five emitters are embedded in PDMS and their wave-guided VIS luminescence feeds crystalline silicon solar cells.
Tetraphenylene-Coated Near-Infrared Benzoselenodiazole Dye: AIE Behavior, Mechanochromism, and Bioimaging
Ye, Fengying,Liu, Yuhong,Chen, Jianhua,Liu, Sheng Hua,Zhao, Wenbo,Yin, Jun
, p. 7213 - 7217 (2019/09/12)
A D-A-D type of tetraphenylene-coating benzoselenodiazole fluorescence dye with near-infrared emission has been designed and constructed. This dye shows an obvious aggregation-induced-emission behavior. In the solid state, it exhibits a reversible mechanochromism with the changes of near-infrared emission. Furthermore, this dye can be used to track the lysosomes of living cells and images in vivo.
Effective modulation of the photoluminescence properties of 2,1,3-benzothiadiazoles and 2,1,3-benzoselenadiazoles by Pd-catalyzed C-H bond arylations
Idris, Imane,Tannoux, Thibault,Derridj, Fazia,Dorcet, Vincent,Boixel, Julien,Guerchais, Veronique,Soulé, Jean-Fran?ois,Doucet, Henri
supporting information, p. 1731 - 1737 (2018/02/23)
A one step procedure towards the synthesis of 4-aryl-2,1,3-benzothiadiazoles, 4,7-diaryl-2,1,3-benzothiadiazoles and 4-aryl-2,1,3-benzoselenadiazoles using palladium-catalyzed regioselective C-H bond arylations of 2,1,3-benzothiadiazole and 2,1,3-benzoselenadiazole was developed. A donor-acceptor compound was also synthesized via two successive C-H bond arylations at C4 and C7 positions of the 2,1,3-benzothiadiazole unit. One of the major achivements of this methodology arises from the fine modulation of the fluorescence wavelength with emission colors covering blue to red regions of the visible spectrum by the simple introduction of the suitable aryl group on the 2,1,3-benzothiadiazole unit.