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:

99.0% ^*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

Circular dichroism and circularly polarized luminescence triggered by self-assembly of tris(phenylisoxazolyl)benzenes possessing a perylenebisimide moiety

10.1039/c2cc31512b

The research focuses on the self-assembly of chiral tris(phenylisoxazolyl)benzenes containing a perylenebisimide (PBI) moiety, which form helical stacks exhibiting strong circular dichroism (CD) and circularly polarized luminescence (CPL) controlled by external stimuli such as solvent properties, temperature, and concentration. The experiments involved synthesizing the chiral compounds, followed by analyses using 1H NMR and UV–vis absorption spectroscopy to study their self-assembling behavior and the resulting optical properties. The 1H NMR spectra revealed concentration-dependent shifts indicating the formation of stacked assemblies, while UV–vis absorption demonstrated the influence of temperature and solvent on the absorption characteristics. The CD spectra showed a mirror image relationship between the chiral assemblies, and CPL measurements confirmed the emission properties of the assemblies in different solvents, highlighting the unique chiroptical properties induced by the self-assembly process.