133546-50-6

Upstream product

• 581-43-1 2.6-dihydroxynaphthalene 
• 133546-47-1 naphtho<1,2-c:5,6-c'>bis<1,2,5>thiadiazole 
• 1467776-41-5 5,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphtho[1,2-c:5,6-c']bis([1,2,5]thiadiazole) 
• 133546-43-7 1,3,5,7-tetrabromo-2,6-dihydroxynaphthalene 

Relevant academic research and scientific papers

Design and synthesis of copolymers of indacenodithiophene and naphtho[1,2- c:5,6- c ]bis(1,2,5-thiadiazole) for polymer solar cells

Three donor-acceptor type of narrow band gap conjugated polymers with enlarged coplanar skeleton were synthesized via Stille copolymerization of indacenodithiophene (IDT) and naphtho[1,2-c:5,6-c]bis(1,2,5-thiadiazole) (NT) based monomers. The energy levels, absorption spectra and band gaps of the resulting polymers were well tuned by utilizing different thiophene derivatives as spacer between IDT and NT units, and polymer PIDT-C12NT which employed bithiophene attached with dodecyl side chain as spacer exhibited superior properties compared to the other two copolymers. All polymers exhibited deep highest occupied molecular orbital energy levels and subsequently lead to high open circuit voltages of fabricated solar cell devices. Best performance of the bulk-heterojunction solar cells with a power conversion efficiency of 5.05% was achieved with PIDT-C12NT as donor and (6,6)-phenyl-C71-butyric acid methyl ester (PC71BM) as acceptor, which can be attributed to its higher charge carrier mobility, the optimized interpenetrating network as well as enhanced absorption coefficient of photoactive layer with respect to the other two polymers. The results demonstrated that the combination of IDT and NT with appropriate spacers was a promising molecular design strategy for the application of solar cells.

Enhanced Donor–π–Acceptor Character of a Porphyrin Dye Incorporating Naphthobisthiadiazole for Efficient Near-Infrared Light Absorption

Donor–π–acceptor (D–π–A) molecules play an important role in various fields including polymer solar cells (PSCs) and dye-sensitized solar cells (DSSCs). In PSCs, naphtho[1,2-c:5,6-c′]bis[1,2,5]thiadiazole (NTz) has emerged as a promising acceptor owing to its higher electron-accepting ability compared with 2,1,3-benzothiadiazole (BT), which is a widely used acceptor unit in DSSCs as well as PSCs. On the other hand, various D–π–A-type porphyrin dyes have been developed for use in DSSCs and have achieved high power conversion efficiencies (η). Given that enhanced D–π–A character improves light-harvesting ability in the near-infrared (NIR) region, we have designed and synthesized for the first time a novel D–π–A-type porphyrin sensitizer, ZnPNTz, incorporating the NTz unit. The porphyrin ZnPNTz shows excellent absorption in the NIR region together with a large Stokes shift as a result of the NTz moiety. A DSSC fabricated with ZnPNTz exhibits photocurrent generation at wavelengths up to 860 nm. Therefore, we have demonstrated that the NTz unit is a promising electron-acceptor unit for novel D–π–A small molecules exhibiting unique optical properties in the NIR region.

NAPHTHOBISTHIADIAZOLE DERIVATIVE

A naphthobisthiadiazole derivative is represented by Formula 1. In Formula 1, Z is selected from a hydrogen atom, a boronic acid group, a boronic acid ester group, a trifluoroborate salt group and a triolborate salt group, and at least one Z is a boronic acid group, a boronic acid ester group, a trifluoroborate salt group or a triolborate salt group. The naphthobisthiadiazole derivative is an organoboron compound, and can be converted to various compounds by a Suzuki-Miyaura coupling reaction; thus, is applicable as a precursor of complex compounds. Using the naphthobisthiadiazole derivative, research, development, and practical applications of low molecular weight compounds and high-molecular compounds useful for various organic semiconductor materials and the like can be ensured.

Donor-acceptor conjugated polymer based on naphtho[1,2- c:5,6- c ]bis[1,2,5]thiadiazole for high-performance polymer solar cells

Donor-acceptor conjugated polymers PBDT-DTBT and PBDT-DTNT, based on 2,1,3-benzothiadiazole (BT) and naphtho[1,2-c:5,6-c]bis[1,2,5]thiadiazole (NT), have been designed and synthesized for polymer solar cells. NT contains two fused 1,2,5-thiadiazole rings that lower the band gap, enhance the interchain packing, and improve the charge mobility of the resulting polymer. Consequently, the NT-based polymer PBDT-DTNT exhibited considerably better photovoltaic performance with a power conversion efficiency (PCE) of 6.00% when compared with the BT-based polymer PBDT-DTBT, which gave a PCE of 2.11% under identical device configurations.

Sulfur Nitride in Organic Chemistry. Part 19. Selective Formation of Benzo- and Benzobisthiadiazole Skeleton in the Reaction of Tetrasulfur Tetranitride with Naphthalenols and Related Compounds

Tetrasulfur tetranitride (N4S4) reacted with 2-naphthols to afford naphthothiadiazoles (13) in high yields, while 1-naphthols gave naphtholbisthiadiazoles as a major product, together with a small amount of 13.In the reactions with naphthalenediols such as 1,5-, 2,6-, 2,7-, 1,6-, and 1,7-diol, naphtho- or naphthobisthiadiazoles were obtained in varying yields.In some cases, naphthotristhiadiazole was formed as a by-product.In reaction with 5-isoquinolinol, 8-quinolinoles,9H-carbazol-2-ol, and dibenzofuran-2-ol, one and/or two 1,2,5-thiadiazole-ringfused heteroaromatic compounds were obtained.