1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride

• CAS: 156028-30-7
• Catalog Number: ACM156028307
• Category: Main Products
• Molecular Weight: 985.14
• Molecular Formula: C64H56O10

Case Study

1,6,7,12-Tetra-Tert-Butylphenoxyperylene-3,4,9,10-Tetracarboxylic Dianhydride for the Synthesis of PDI-Bridged Step-Type Polysiloxanes

Fu, Wenxin, et al. Macromolecules, 2011, 44(2), 203-207.

Soluble perylene diimide (PDI)-bridged ladder polysiloxanes (PDI-LPS) were prepared by directional dehydration polycondensation of ladder superstructures (LS). Starting with 1,6,7,12-tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride (1), stepwise the tetrafunctional precursor M2 was made. M2 self-assembled as ladder superstructures (LS) by hydrogen bonding and π-π stacking. The supramolecular LS served as both a polymerization precursor and a template to form ladder polysiloxanes (LPS).
Synthesis procedure of the tetrafunctional precursor
· 1,6,7,12-Tetra-tert-butylphenoxyperylene-N,N'-bis(3-aminopropylmethyldiethoxysilane)-3,4,9,10-tetracarboxylic Dianhydride (M1): Compound M1 was prepared by reaction of 1,6,7,12-tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride (1) with 3-aminopropylmethyldiethoxysilane (2) in dry ethanol under inert argon conditions. Reaction solution was refluxed for 10 hours, and the solution filtered and purified by flash chromatography on silica gel. This made 1.95 g of M1 as a dark red solid in 60% yield.
· 1,6,7,12-Tetra-tert-butylphenoxyperylene-N, N'-bis(3-aminopropylmethyldihydroxylsilane)-3,4,9,10-tetracarboxylic Dianhydride (M2): Compound M2 was created by hydrolysis of M1. M1 was dissolved in a mixture of THF and water, and the reaction was initiated by adding a small amount of hydrochloric acid at 0 °C. The progress of the hydrolysis was monitored using thin-layer chromatography. After 6 hours, the reaction was quenched, and the product was extracted with diethyl ether, dried, and precipitated with hexane. This gave 800 mg of M2 in the form of a dark red powder (87.5% yield).

Synthesis of Perylenecarboxylic Diimide-Bridged Triethoxysilane (PDI-Sil) from 1,6,7,12-Tetra-Tert-Butylphenoxyperylene-3,4,9,10-Tetracarboxylic Dianhydride for LSCs

Meazzini, Ilaria, et al. Journal of Materials Chemistry C, 2016, 4(18), 4049-4059.

This paper discussed the strategic design of ureasil-type hybrid materials featuring a π-conjugated perylene carboxdiimide-coupled triethoxysilane (PDI-Sil), which is covalently integrated into the siliceous framework. Perylene carboxdiimides are commonly used as model lumophores in luminescent solar concentrators (LSCs) owing to their strong molar absorption coefficients, remarkable photoluminescent quantum yields, and high photostability. The key raw material for synthesizing PDI-Sil is 1,6,7,12-tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride.
Synthesis of PDI-Sil
To obtain N,N-bis(3-triethoxysilylpropyl)-1,6,7,12-tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxdiimide (PDI-Sil), 1,6,7,12-tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride (503 mg, 0.51 mmol) was put in a Schlenk flask with 150 mL dry ethanol. Then added 3-aminopropyltriethoxysilane (1.45 mL, 6.12 mmol, 12 equivalents) dropwise. It was refluxed for two days and then cooled to room temperature, the precipitate was filtered and thoroughly washed with cold ethanol to eliminate excess 3-aminopropyltriethoxysilane.

Custom Q&A

What is the molecular formula of 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride?

The molecular formula is C64H56O10.

What are some synonyms for 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride?

Some synonyms include 156028-30-7, 11,14,22,26-tetrakis(4-tert-butylphenoxy)-7,18-dioxaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone, and 5,6,12,13-tetrakis(4-(tert-butyl)phenoxy)anthra[2,1,9-def:6,5,10-d'e'f']diisochromene-1,3,8,10-tetraone.

What is the molecular weight of 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride?

The molecular weight is 985.1 g/mol.

When was 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride created?

It was created on February 7, 2007.

When was 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride last modified?

It was last modified on October 21, 2023.

What is the IUPAC name of 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride?

The IUPAC name is 11,14,22,26-tetrakis(4-tert-butylphenoxy)-7,18-dioxaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(22),2(26),3,5(25),9,11,13,15,20,23-decaene-6,8,17,19-tetrone.

What is the InChI of 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride?

The InChI is InChI=1S/C64H56O10/c1-61(2,3)33-13-21-37(22-14-33)69-45-29-41-49-42(58(66)73-57(41)65)31-47(71-39-25-17-35(18-26-39)63(7,8)9)53-54-48(72-40-27-19-36(20-28-40)64(10,11)12)32-44-50-43(59(67)74-60(44)68)30-46(52(56(50)54)51(45)55(49)53)70-38-23-15-34(16-24-38)62(4,5)6/h13-32H,1-12H3.

What is the InChIKey of 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride?

The InChIKey is OIBUEAFZCMYHPY-UHFFFAOYSA-N.

What is the Canonical SMILES of 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride?

The Canonical SMILES is CC(C)(C)C1=CC=C(C=C1)OC2=C3C4=C(C=C5C6=C4C(=C(C=C6C(=O)OC5=O)OC7=CC=C(C=C7)C(C)(C)C)C8=C(C=C9C(=C38)C(=C2)C(=O)OC9=O)OC1=CC=C(C=C1)C(C)(C)C)OC1=CC=C(C=C1)C(C)(C)C.

What is the Heavy Atom Count of 1,6,7,12-Tetra-tert-butylphenoxyperylene-3,4,9,10-tetracarboxylic dianhydride?

The Heavy Atom Count is 74.