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Chemical Structure| 2243-67-6

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Zawadzka, Magdalena ; Nitschke, Pawel ; Musiol, Marta ; Siwy, Mariola ; Pluczyk-Malek, Sandra ; Honisz, Damian , et al.

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 [ 2243-67-6 ]

CAS No. :2243-67-6
Formula : C10H10N2
M.W : 158.20
SMILES Code : NC1=CC=C2C=C(N)C=CC2=C1
MDL No. :MFCD01109656
InChI Key :GOGZBMRXLADNEV-UHFFFAOYSA-N
Pubchem ID :2749139

Safety of [ 2243-67-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 2243-67-6 ]

* 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 [ 2243-67-6 ]
 

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