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[ CAS No. 2243-62-1 ] {[proInfo.proName]}

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Chemical Structure| 2243-62-1
Chemical Structure| 2243-62-1
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Product Citations

Product Citations

Zawadzka, Magdalena ; Nitschke, Pawel ; Musiol, Marta , et al. DOI: PubMed ID:

Abstract: Electrochromism of organic compounds is a well-known phenomenon; however, nowadays, most research is focused on anodic coloring materials. Development of efficient, cathodic electrochromic materials is challenging due to the worse stability of electron accepting materials compared with electron donating ones. Nevertheless, designing stable cathodic coloring organic materials is highly desired-among other reasons-to increase the coloration performance. Hence, four phthalimide derivatives named 1,5-PhDI, 1,4-PhDI, 2,6-PhDI and 3,3-PhDI were synthesized and analyzed in depth. In all cases, two imide groups were connected via naphthalene (1,5-PhDI, 1,4-PhDI, 2,6-PhDI) or 3,3-dimethylnaphtidin (3,3-PhDI) bridge. To observe the effect of chem. structure on physicochem. properties, various positions of imide bond were considered, namely, 1,5- 1,4- and 2,6-. Addnl., a compound with the pyromellitic diimide unit capped with two 1-naphtalene substituents was obtained. All compounds were studied in terms of their thermal behavior, using differential calorimetry (DSC) and thermogravimetric anal. (TGA). Moreover, electrochem. (CV, DPV) and spectroelectrochem. (UV-Vis and EPR) analyses were performed to evaluate the obtained materials in terms of their application as cathodic electrochromic materials. All obtained materials undergo reversible electrochem. reduction which leads to changes in their optical properties. In the case of imide derivatives, absorption bands related to both reduced and neutral forms are located in the UV region. However, importantly, the introduction of the 3,3-dimethylnaphtidine bridge leads to a noticeable bathochromic shift of the reduced form absorption band of 3,3-PhDI. This indicates that optimization of the phthalimide structure allows us to obtain stable, cathodic electrochromic materials.

Keywords: electrochemistry ; spectroelectrochemistry ; electrochromism ; phthalimides

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Product Details of [ 2243-62-1 ]

CAS No. :2243-62-1 MDL No. :MFCD00004029
Formula : C10H10N2 Boiling Point : -
Linear Structure Formula :(H2N)2C10H6 InChI Key :KQSABULTKYLFEV-UHFFFAOYSA-N
M.W : 158.20 Pubchem ID :16720
Synonyms :

Calculated chemistry of [ 2243-62-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.76
TPSA : 52.04 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : 0.89
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 1.88
Log Po/w (SILICOS-IT) : 1.53
Consensus Log Po/w : 1.51

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.0
Solubility : 1.59 mg/ml ; 0.01 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 4.28 mg/ml ; 0.0271 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.34
Solubility : 0.072 mg/ml ; 0.000455 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 2243-62-1 ]

Signal Word:Danger Class:9
Precautionary Statements:P201-P202-P264-P270-P280-P301+P312-P308+P313-P330-P403-P501 UN#:3077
Hazard Statements:H302-H350-H411 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2243-62-1 ]

* 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 [ 2243-62-1 ]

[ 2243-62-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 652-12-0 ]
  • [ 2243-62-1 ]
  • 2,2'-(naphthalene-1,5-diyl)bis(4,5,6,7-tetrafluoroisoindoline-1,3-dione) [ No CAS ]
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