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Chemical Structure| 2554-06-5 Chemical Structure| 2554-06-5
Chemical Structure| 2554-06-5

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CAS No.: 2554-06-5

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Shu, Haonian ; Khlyustova, Alexandra ; Park, Kwang‐Won ; Stafslien, Shane ; Kang, Gyeongwan ; Chen, Pengyu , et al.

Abstract: Biofouling, the accumulation of living organisms on submerged surfaces, remains a critical challenge in marine and industrial settings. Amphiphilic coatings offer promising antifouling performance by presenting both hydrophilic and hydrophobic domains, but often rely on environmentally persistent perfluoroalkyl substances (PFAS). This study introduces a fluorine-free amphiphilic copolymer synthesized via initiated Chemical Vapor Deposition (iCVD), incorporating 1,3,5,7-tetramethyl-1,3,5,7-tetravinyl cyclotetrasiloxane (V4D4) as the hydrophobic component and pyridinium-based zwitterions as the hydrophilic moiety. V4D4 enables an unprecedented conversion rate of pyridine to zwitterionic sulfobetaine, reaching 69.5% at a 240 nm depth into the film from a diffusion-limited vapor derivatization reaction, pointing to the network flexibility afforded by V4D4. The coating reduces Pseudomonas aeruginosa attachment by over 90% compared to aluminum surfaces and decreases Cellulophaga lytica biofilm formation by 55% compared to a zwitterionic benchmark under dynamic flow. Against the model diatom Navicula incerta, it achieves 99.7% removal after water jetting, outperforming a commercial fouling-release paint, Intersleek? 1100SR. The high fouling-release performance is attributed to its low Young’s modulus, promoting deformation under shear. Additionally, the coating exhibits chemical stability in alkaline conditions that degrade PFAS-based counterparts. These findings present a durable, high-performance, and environmentally responsible alternative to PFAS-based amphiphilic copolymers as the next-generation antifouling technologies.

Keywords: amphiphilic polymer ; antifouling materials ; biofouling ; initiated chemical vapor deposition ; marine fouling ; PFAS

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Pengyu Chen ; Zheyuan Zhang ; Kwang Won Park ; Christina H. Yu ; Rong Yang ;

Abstract: Initiated chemical vapor deposition (iCVD) has revolutionized the preparation of high-quality conformal polymer films with excellent control over composition and properties at the nanoscale. It is compatible with over 70 functional monomers . Despite that chemical versatility, side reactions during iCVD are not well understood. For example, chain transfer could happen during the propagation of an important class of monomers that contain nitrogen (N), arresting the polymerization and limiting the molecular weight. Here, we use (1VI) to demonstrate the chain transfer reaction to the group during iCVD, which leads to unpredictable deposition kinetics, low molecular weight, and undesirable products. We further introduce a strategy that utilizes a vapor solvent to engineer monomer reactivity and suppress side reactions. By replacing the traditional patch flow, Ar, with (AcOH), which forms hydrogen bonding with 1VI, chain transfer is suppressed, and the deposition rate is increased by as much as 280% while restoring its linear dependence on the monomer partial pressure. That linear dependence has not been achieved previously for 1VI. The tunable deposition kinetics, in turn, leads to a broader range of attainable material properties, including nearly doubling the maximum attainable molecular weight (from 8 kDa to 16 kDa) and increasing the elastic modulus (from 3.5 to 4.7 GPa). The vapor solvent is also effective at suppressing chain transfer in other N-containing monomers , like (2-dimethylamine) ethyl methacrylate (DMAEMA), leading to a considerable increase in the molecular weight (from 16 kDa to 38 kDa). The vapor solvent selectively increases the reactivity of N-containing monomers during copolymerization, demonstrated using 1VI and divinylbenzene (DVB) or 1,3,5,7-tetravinyl tetramethylcyclotetrasiloxane (V4D4), increasing the reactivity ratio of 1VI by an order of magnitude according to the Fineman–Ross equation. This robust strategy engineers monomer reactivity without the need for chemical modifications. It improves the chemical precision of iCVD polymerization, particularly for an important class of N-containing monomers , which have found broad applications as the polymer–electrolyte interphase in batteries, antifouling coatings in food and water production, and bioactive and functionalizable coatings in sensors.

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Chen, Pengyu ; Shu, Harry ; Tang, Wenjing ; Yu, Christina ; Yang, Rong ;

Abstract: Biofouling represents a critical challenge in marine transportation, healthcare, and food manufacturing, among other industries, as it promotes contamination and increases maintenance costs. Zwitterionic polymers, known for their exceptional antifouling properties, offer a promising solution for biofouling deterrence. Despite the rapid development of zwitterionic polymers in recent years, the design rules, especially concerning the choice of cationic moieties to optimize biofouling deterrence, remain elusive. In this study, we leveraged a versatile all-dry synthesis scheme to achieve a selection of 9 zwitterionic polymers, 5 of which are unprecedented for this synthesis paradigm, thus systematically unraveling that molecular design rule. Notably, we developed a synthesis strategy to enable nanoscale compositional gradient along the coating cross-section, which ensures the robustness of the zwitterionic polymer coatings irrespective of the choice of cation-anion combinations. That robustness is enabled by an organosilicon-based layer at the coating-substrate interface, which simultaneously enhances coating adhesion and chemical stability while ensuring high concentration of zwitterionic moieties at the polymer-liquid interface to maximize biofouling deterrence. The antifouling efficacy was assessed using biofilms of Pseudomonas aeruginosa or Bacillus subtilis. All coatings demonstrated antifouling efficacy, with a novel zwitterionic polymer comprising a combination of imidazolium and carboxyl groups achieving the greatest antibiofilm effects, which we attributed to the strong hydration. This study highlights the coating architecture, i.e., one with nanoscale gradient and varying crosslinking densities, as a valid strategy to render zwitterionic polymers robust coatings and the imidazolium-based carboxybetaine as a promising next-generation antibiofouling chemistry.

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Przybylak, Marcin ; Przybylska, Agnieszka ; Szymanska, Anna ; Maciejewski, Hieronim ;

Abstract: During this study four different methods of hydrophobization of cotton textiles via thiol-ene click reaction were compared. It was hypothesized that the same products would be obtained in all cases, albeit in different ways. During synthesis of hydrophobic compounds 2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetrasiloxane (D4Vi), (3-mercaptopropyl)trimethoxysilane (M) and alkyl thiols of various alkyl chain lengths (C6H13SH(C6), C8H17SH(C8), C10H21SH(C10), C12H25SH(C12), C18H37SH(C18)) were used as a substrates. Some of the modifiers were synthesized via thiol-ene click reaction and then introduced to the cotton textile via a sol-gel process. The remaining modifiers were synthesized via thiol-ene click reaction directly on to cotton textiles. The influence of alkyl chain lengths on the hydrophobic effect were also investigated. Hydrophobization of cotton textile was evaluated through measurement of water contact angle. Addnl., the surface of the cotton textile was also examined via IR anal., scanning electron microscope (SEM), and elemental anal. (SEM-EDS). As a result of this study a superhydrophobic cotton textile was obtained. The research showed the significant influence of the type of modification method via thiol-ene click reaction on the hydrophobicity of cotton textiles.

Keywords: Thiol-ene click ; Cotton textiles ; Hydrophobization ; Organosilicon ; Cyclic siloxane

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Alternative Products

Product Details of [ 2554-06-5 ]

CAS No. :2554-06-5
Formula : C12H24O4Si4
M.W : 344.66
SMILES Code : C=C[Si]1(O[Si](C)(O[Si](C)(O[Si](C)(O1)C=C)C=C)C=C)C
MDL No. :MFCD00040293
InChI Key :VMAWODUEPLAHOE-UHFFFAOYSA-N
Pubchem ID :75706

Safety of [ 2554-06-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319
Precautionary Statements:P305+P351+P338

Calculated chemistry of [ 2554-06-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 20
Num. arom. heavy atoms 0
Fraction Csp3 0.33
Num. rotatable bonds 4
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 91.6
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

36.92 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

4.17
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

5.8
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.26
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.08
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.7
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.29

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-5.37
Solubility 0.00148 mg/ml ; 0.0000043 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-6.35
Solubility 0.000156 mg/ml ; 0.000000452 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Poorly soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.55
Solubility 0.974 mg/ml ; 0.00282 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-4.28 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 5.67

Application In Synthesis of [ 2554-06-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 2554-06-5 ]

[ 2554-06-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 52092-47-4 ]
  • [ 2554-06-5 ]
  • [ 125889-39-6 ]
  • 2
  • [ 2554-06-5 ]
  • [ 13040-77-2 ]
  • [ 79964-37-7 ]
  • 3
  • [ 2488-01-9 ]
  • [ 2554-06-5 ]
  • C52H96O4Si12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With platinum; In toluene; at 119 - 130℃; for 48h; (1) taking 0.5 g of hydrosilylation catalyst platinum, diluted with 5 mL of toluene, and then added to a 250 mL three-necked flask;(2) Take 3.45 g of tetramethyltetravinylcyclotetrasiloxane (tetramethyl-)Tetravinylcyclotetrasiloxane, molecular weight MW=345g/mol), diluted with 20mL of toluene and added to the three-neckedBottle(3) Take 11.66g of <strong>[2488-01-9]1,4-bis(dimethylsilyl)benzene</strong> (1,4-Bis(dimethylsilyl)benzene,Sub-quantity = 194.42), diluted with 25 mL of toluene and added to a three-necked flask;(4) Set the oil bath temperature to 130 C, turn on the stirring, and turn on the condensed water until the temperature in the three-necked flask is 119 C.The mixture should start to reflux;(5) After refluxing for a period of time, take a small amount of the reaction mixture for IR test to determine whether the reaction is completed.all.(6) After 48 hours, the IR results showed that the carbon-free carbon double bond absorption peak indicates the end of the reaction, and the 1H NMR results showed noVinyl H, at this time, the reaction mixture was transferred to a rotary evaporator to distill off the solvent, and the product crosslinker 4 was precipitated
 

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