Production Method 1

211737-28-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -70 °C; 45 min, -70 °C
1.2 -70 °C → 25 °C; 18 h, 25 °C
1.3 Solvents: Methanol

Reference

A Trisheteroleptic Cyclometalated RuII Sensitizer that Enables High Power Output in a Dye-Sensitized Solar Cell

Bomben, Paolo G.; Gordon, Terry J.; Schott, Eduardo; Berlinguette, Curtis P., Angewandte Chemie, 2011, 50(45), 10682-10685

Production Method 2

18794-77-9

25015-63-8

917985-54-7

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Hexane ;  5 min, rt
1.2 overnight, 50 °C

Reference

Reticulated Heterojunctions for Photovoltaic Devices

Gorodetsky, Alon A.; Chiu, Chien-Yang; Schiros, Theanne; Palma, Matteo; Cox, Marshall; et al, Angewandte Chemie, 2010, 49(43), 7909-7912

Production Method 3

211737-28-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 1 h, -78 °C
1.2 2 h, -78 °C; overnight, -78 °C → rt
1.3 Solvents: Water

Reference

Fluorescent organic nanoparticles based on branched small molecule: preparation and ion detection in lithium-ion battery

Wang, Jinshan; Xu, Xinjun; Shi, Leilei; Li, Lidong, ACS Applied Materials & Interfaces, 2013, 5(8), 3392-3400

Production Method 4

211737-28-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: Dichlorobis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  16 h, reflux

Reference

Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties

Arakawa, Yuki; Kang, Sungmin; Nakajima, Shunpei; Sakajiri, Koichi; Kawauchi, Susumu; et al, Liquid Crystals, 2014, 41(5), 642-651

Production Method 5

18794-77-9

25015-63-8

917985-54-7

Reaction Conditions

1.1 Catalysts: Bis[(1,2,5,6-η)-1,5-cyclooctadiene]di-μ-methoxydiiridium ,  4,4′-Bis(1,1-dimethylethyl)-2,2′-bipyridine Solvents: Hexane ;  5 min, rt
1.2 8 - 12 h, 50 °C

Reference

Shape-shifting in contorted dibenzotetrathienocoronenes

Chiu, Chien-Yang; Kim, Bumjung; Gorodetsky, Alon A.; Sattler, Wesley; Wei, Sujun; et al, Chemical Science, 2011, 2(8), 1480-1486

Production Method 6

211737-28-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: tert-Butyllithium Solvents: Pentane ,  Tetrahydrofuran ;  2 h, -78 °C
1.2 0.2 h, -78 °C; -78 °C → rt; 20 h, rt

Reference

Soluble and Easily Crystallized Anthracene Derivatives: Precursors of Solution-Processable Semiconducting Molecules

Park, Jong-Hwa; Chung, Dae Sung; Park, Jong-Won; Ahn, Taek; Kong, Hoyoul; et al, Organic Letters, 2007, 9(13), 2573-2576

Production Method 7

18794-77-9

25015-63-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -78 °C; -78 °C → 0 °C; 20 min, 0 °C; 0 °C → -78 °C
1.2 -78 °C; 17 h, rt

Reference

Tris(thiocyanate) Ruthenium(II) Sensitizers with Functionalized Dicarboxyterpyridine for Dye-Sensitized Solar Cells

Yang, Shen-Han; Wu, Kuan-Lin; Chi, Yun; Cheng, Yi-Ming; Chou, Pi-Tai, Angewandte Chemie, 2011, 50(36), 8270-8274

Production Method 8

211737-28-9

73183-34-3

917985-54-7

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Dimethylformamide ;  overnight, 80 °C

Reference

Orthogonal Functionalization of Cyclopenta[hi]aceanthrylenes

Lee, Che-Hsiung; Plunkett, Kyle N., Organic Letters, 2013, 15(6), 1202-1205

Production Method 9

18794-77-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium
1.2 Solvents: Tetrahydrofuran ;  -78 °C → rt

Reference

In search of efficient solubilizing groups for liquid and luminescent oligo(phenylene-thiophene) chromophores

Luponosov, Yuriy N.; Balakirev, Dmitry O.; Dyadishchev, Ivan V.; Solodukhin, Alexander N.; Obrezkova, Marina A.; et al, Journal of Materials Chemistry C: Materials for Optical and Electronic Devices, 2020, 8(47), 17074-17082

Production Method 10

18794-77-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -78 °C; 2 h, -78 °C
1.2 overnight, rt
1.3 Reagents: Water ;  cooled

Reference

Synthesis and characterization of starburst conjugated molecules with multiple p-n branches for narrow band gap modulation

Zhao, Lingling; Jiu, Yuanda; Wang, Jianyun; Zhang, Xinwen; Lai, Wenyong; et al, Huaxue Xuebao, 2013, 71(9), 1248-1256

Production Method 11

18794-77-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 2 h, -78 °C
1.2 -78 °C; -78 °C → rt; overnight, rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Peripherally diketopyrrolopyrrole-functionalized dendritic oligothiophenes - synthesis, molecular structure, properties and applications

Gao, Wei; Luo, Qun; Wang, Junkai; Lin, Yi; Tang, Changquan; et al, Polymer Chemistry, 2017, 8(9), 1460-1476

Production Method 12

211737-28-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -78 °C; 1 h, -78 °C
1.2 15 min, -78 °C; -78 °C → rt; 18 h, rt

Reference

Behaviour of Regioisomeric Bithiophenes in the Oxidative Synthesis of Tetrathieno-Fused π-Expanded Fluorenes and Their Characterization

Jagarapu, Ramakrishna; Maddala, Sudhakar; Mahto, Indrajit; Venkatakrishnan, Parthasarathy, Asian Journal of Organic Chemistry, 2020, 9(12), 2144-2152

Production Method 13

18794-77-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C → rt; 25 - 30 min, rt; rt → -78 °C
1.2 3 h, -78 °C

Reference

Ligand Engineering for the Efficient Dye-Sensitized Solar Cells with Ruthenium Sensitizers and Cobalt Electrolytes

Aghazada, Sadig; Gao, Peng; Yella, Aswani; Marotta, Gabriele; Moehl, Thomas; et al, Inorganic Chemistry, 2016, 55(13), 6653-6659

Production Method 14

18794-77-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C → 0 °C; 20 min, 0 °C
1.2 -78 °C → rt; 3 h, rt

Reference

Dye Molecular Structure Device Open-Circuit Voltage Correlation in Ru(II) Sensitizers with Heteroleptic Tridentate Chelates for Dye-Sensitized Solar Cells

Wu, Kuan-Lin; Li, Cheng-Hsuan; Chi, Yun; Clifford, John N.; Cabau, Lydia; et al, Journal of the American Chemical Society, 2012, 134(17), 7488-7496

Production Method 15

18794-77-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -78 °C; 30 min, -78 °C; -78 °C → rt; 1 h, rt; rt → -78 °C
1.2 -78 °C; -78 °C → rt; overnight, rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  -78 °C

Reference

A detailed study on the thermal, photo-physical and electrochemical properties and OFET applications of D-π-A-π-D structured unsymmetrical diketopyrrolopyrrole materials

Bharath, D.; Chithiravel, S.; Sasikumar, M.; Chereddy, Narendra Reddy; Shanigaram, Balaiah; et al, RSC Advances, 2015, 5(115), 94859-94865

Production Method 16

76-09-5

18794-77-9

917985-54-7

Reaction Conditions

1.1 Reagents: Dimethyl-p-toluidine ,  Aluminum chloride ,  Boron trichloride Solvents: Dichloromethane ;  10 min, rt; 18 h, rt
1.2 Reagents: Triethylamine ;  rt

Reference

Simple inexpensive boron electrophiles for direct arene borylation

Del Grosso, Alessandro; Helm, Matthew D.; Solomon, Sophia A.; Caras-Quintero, Dolores; Ingleson, Michael J., Chemical Communications (Cambridge, 2011, 47(46), 12459-12461

Production Method 17

211737-28-9

61676-62-8

917985-54-7

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -78 °C

Reference

Aggregation-induced Emission and Aggregation Promoted Photo-oxidation in Thiophene-substituted Tetraphenylethylene Derivative

Zhu, Linna; Wang, Rui; Tan, Luxi; Liang, Xianfeng; Zhong, Cheng; et al, Chemistry - An Asian Journal, 2016, 11(20), 2932-2937

Production Method 18

211737-28-9

61676-62-8

917985-54-7

Reaction Conditions

Reference

Molecularly Engineered Ru(II) Sensitizers Compatible with Cobalt(II/III) Redox Mediators for Dye-Sensitized Solar Cells

Wu, Kuan-Lin; Huckaba, Aron J.; Clifford, John N.; Yang, Ya-Wen; Yella, Aswani; et al, Inorganic Chemistry, 2016, 55(15), 7388-7395

2-(5-hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Raw materials

• 2,3-Dimethylbutane-2,3-diol
• 2-Hexylthiophene
• 5-Bromo-2-hexylthiophene
• 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Bis(pinacolato)diborane
• Pinacolborane

2-(5-hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation Products

• 2-(5-hexyl-2-thienyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (917985-54-7)

• 1. Fe3O4 nanoparticle chains with N-doped carbon coating: magnetotactic bacteria assisted synthesis and high-rate lithium storage?
  Dan Yang,Yanping Zhou,Xianhong Rui,Jixin Zhu,Ziyang Lu,Eileen Fong,Qingyu Yan RSC Adv., 2013,3, 14960-14962
• 2. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
  Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
• 3. Distinct roles of SNARE-mimicking lipopeptides during initial steps of membrane fusion?
  Alena Koukalová,?árka Pokorná,Aimee L. Boyle,Nestor Lopez Mora,Alexander Kros,Martin Hof,Radek ?achl Nanoscale, 2018,10, 19064-19073
• 4. Etching of glass microchips with supercritical water?
  Pavel Karásek,Jakub Grym,Michal Roth,Josef Planeta,Franti?ek Foret Lab Chip, 2015,15, 311-318
• 5. Esterase-responsive polymeric prodrug-based tumor targeting nanoparticles for improved anti-tumor performance against colon cancer?
  Gang Pan,Yi-jie Bao,Jie Xu,Tao Liu,Cheng Liu,Yan-yan Qiu,Xiao-jing Shi,Hui Yu,Ting-ting Jia,Xia Yuan,Ze-ting Yuan,Yi-jun Cao RSC Adv., 2016,6, 42109-42119

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Thiophenes 2,5-disubstituted thiophenes

• 1361117-06-7(2-(5''-(2-Ethylhexyl)-[2,2':5',2''-terthiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1447710-10-2(5-Ethylthiophene-2-boronic acid pinacol ester)
• 851298-69-6(1,3,2-Dioxaborolane,2-(5''-hexyl[2,2':5',2''-terthiophen]-5-yl)-4,4,5,5-tetramethyl-)
• 1402166-55-5(2-(5-cyclohexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 925424-90-4(4,4,5,5-Tetramethyl-2-(5-octyl-2-thienyl)-1,3,2-dioxaborolane)
• 1390584-88-9(2-[5-(2-Ethylhexyl)thiophen-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 1473358-18-7(5-N-Propylthiophene-2-Boronic Acid Pinacol Este)
• 1338083-26-3(2-(5-Butylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 579503-59-6(2-(5'-Hexyl-2,2'-bithiophen-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
• 476004-80-5(4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane)