2,9-Di(pentan-3-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone

Base Information

• Chemical Name: 2,9-Di(pentan-3-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone
• CAS No.: 110590-81-3
• Molecular Formula: C34H30 N2 O4
• Molecular Weight: 530.623
• European Community (EC) Number: 682-826-7
• DSSTox Substance ID: DTXSID10553714
• Nikkaji Number: J1.376.371B
• Wikidata: Q82434372
• Mol file: 110590-81-3.mol

Synonyms:110590-81-3;2,9-Di(pentan-3-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone;2,9-Di(pent-3-yl)anthra2,1,9-def;7,18-di(pentan-3-yl)-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone;SCHEMBL305590;7-DEAZA-2-DEOXYADENOSINE;DTXSID10553714;2,9-Di(pent-3-yl)anthra2,1,9-def:6,5,10-d'e'f'diisoquinoline-1,3,8,10-tetrone;AS-82289;CS-0110760;F75488;N,N'-Bis(3-pentyl)perylene-3,4,9,10-bis(dicarboximide);n,n'-bis(1-ethylpropyl)-3,4:9,10-perylenebis(dicarboximide);N,N'-Bis(ethylpropyl)perylene-3,4,9,10-tetracarboxylic acid;N,N'-Bis(3-pentyl)perylene-3,4,9,10-bis(dicarboximide), 99% (HPLC);N,N inverted exclamation mark -Bis(ethylpropyl)perylene-3,4,9,10-tetracarboxylicdiimide;2,9-Di(pentan-3-yl)isoquinolino[4',5',6':6,5,10]anthra[2,1,9-def]isoquinoline-1,3,8,10(2H,9H)-tetrone;7,18-di(pentan-3-yl)-7,18-diazaheptacyclo[14.6.2.2^{2,5.0^{3,12.0^{4,9.0^{13,23.0^{20,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone

Chemical Property of 2,9-Di(pentan-3-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone

Chemical Property:

• Melting Point: >450°C
• Boiling Point: 724.1±33.0 °C(Predicted)
• PKA: -2.33±0.20(Predicted)
• PSA: 78.14000
• Density: 1.351±0.06 g/cm3(Predicted)
• LogP: 6.68520
• Storage Temp.: 2-8°C
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 530.22055744
• Heavy Atom Count: 40
• Complexity: 928

Purity/Quality:

99% ^*data from raw suppliers

N,N′-Bis(3-pentyl)perylene-3,4,9,10-bis(dicarboximide) 99% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)N1C(=O)C2=C3C(=CC=C4C3=C(C=C2)C5=C6C4=CC=C7C6=C(C=C5)C(=O)N(C7=O)C(CC)CC)C1=O
• Uses: EP-PDI (acceptor) blended with P3HT (donor) and PCBM (donor) can be used in the fabrication of organic photovoltaic devices and organic solar cells. It forms a mixture with tetrahydrofuran (THF) that shows high intensity fluorescence which can be used as a sensor for the detection of nitroaromatic compounds.

Technology Process of 2,9-Di(pentan-3-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone

There total 2 articles about 2,9-Di(pentan-3-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-1,3,8,10(2H,9H)-tetraone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) + 3-aminopentane (616-24-0) → N,N'-bis(1-ethylpropyl)-3,4:9,10-perylenebis(dicarboximide) (110590-81-3)

Guidance literature:

With 1H-imidazole; at 110 ℃; for 24h;

Reference yield:

3-pentanone oxime (1188-11-0) → N,N'-bis(1-ethylpropyl)-3,4:9,10-perylenebis(dicarboximide) (110590-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium-dihydrobis(2-methoxyethoxy)aluminate / toluene / 4 h / 140 °C

2: 46 percent / imidazole / 4 h / 160 °C

With 1H-imidazole; sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene;

Reference yield: 83.0%

5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane (5123-13-7) + N,N'-bis(1-ethylpropyl)-3,4:9,10-perylenebis(dicarboximide) (110590-81-3) → N,N'-bis(1-ethylpropyl)-2,5,8,11-tetraphenylperylene-3,4:9,10-tetracarboxylic acid bisimide (1192464-27-9)

Guidance literature:

With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II); In 3,3-dimethyl-butan-2-one; 1,3,5-trimethyl-benzene; at 140 ℃; for 21h; Inert atmosphere;

DOI:10.1021/ol902271b

upstream raw materials:

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

3-aminopentane

3-pentanone oxime

Downstream raw materials:

perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride

9-(1-ethylpropyl)-1H-2-benzopyrano[6',5',4':10,5,6]anthra[2,1,9-def]isoquinoline-1,3,8,10(9H)-tetraone

N-(1-ethylpropyl)-N'-[(1S)-(2,4-dibromophenoxymethyl)-3-methylbutyl]perylene-3,4:9,10-tetracarboxylic bisimide

N-(1-ethylpropyl)-N'-[(1S)-(2,5-dibromo-4-(2-ethylhexyloxy)phenoxymethyl)-3-methylbutyl]perylene-3,4:9,10-tetracarboxylic bisimide

Refernces

• 1、 Liu, Hongmei,Wang, Yongli,Liu, Chenghui,Li, Hongxia,Gao, Baoxiang,Zhang, Licui,Bo, Fuli,Bai, Qianqian,Ba, Xinwu. "Fluorescent water-soluble probes based on dendritic PEG substituted perylene bisimides: Synthesis, photophysical properties, and live cell images". . p. 6176 - 6181. Retrieved 2012.
• 2、 Mizoshita, Norihiro,Yamanaka, Ken-Ichi,Hiroto, Satoru,Shinokubo, Hiroshi,Tani, Takao,Inagaki, Shinji. "Energy and electron transfer from fluorescent mesostructured organosilica framework to guest dyes". . p. 3987 - 3994. Retrieved 2012.
• 3、 Wang, Helin,Chen, Lingcheng,Xiao, Yi. "Heterologous perylene diimide arrays: Potential non-fullerene acceptors in organic solar cells". . p. 8875 - 8882. Retrieved 2017.
• 4、 Schulze, Marcus,Steffen, Andreas,Würthner, Frank. "Near-IR phosphorescent ruthenium(II) and iridium(III) perylene bisimide metal complexes". . p. 1570 - 1573. Retrieved 2015.
• 5、 Dordevi?, Luka,Milano, Domenico,Demitri, Nicola,Bonifazi, Davide. "O-Annulation to Polycyclic Aromatic Hydrocarbons: A Tale of Optoelectronic Properties from Five- To Seven-Membered Rings". . p. 4283 - 4288. Retrieved 2020.
• 6、 Nazari, Maryam,Cieplechowicz, Edward,Welsh, Thomas A.,Welch, Gregory C.. "A direct comparison of monomeric vs. dimeric and non-annulated vs. N-annulated perylene diimide electron acceptors for organic photovoltaics". . p. 5187 - 5195. Retrieved 2019.
• 7、 Sebastian, Ebin,Hariharan, Mahesh. "Null Exciton-Coupled Chromophoric Dimer Exhibits Symmetry-Breaking Charge Separation". . . Retrieved 2021.
• 8、 Hendsbee, Arthur D.,McAfee, Seth M.,Sun, Jon-Paul,McCormick, Theresa M.,Hill, Ian G.,Welch, Gregory C.. "Phthalimide-based π-conjugated small molecules with tailored electronic energy levels for use as acceptors in organic solar cells". . p. 8904 - 8915. Retrieved 2015.
• 9、 Cheng, Qian,Chen, Zhiyuan,Zhang, Qing,Zhu, Senqiang,Liu, Rui,Zhu, Hongjun. "Synthesis, luminescence, and excited-state absorption properties of disubstituted perylene diimide derivatives modified at bay region". . p. 247 - 254. Retrieved 2021/12/01.