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UV–Vis and ECD spectroelectrochemistry of atropisomeric naphthalenediimide derivative

Version 1.0

Rode, Joanna, 2026, "UV–Vis and ECD spectroelectrochemistry of atropisomeric naphthalenediimide derivative", https://doi.org/10.18150/5WR7XY, RepOD, V1

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Description

The UV–vis and ECD spectroelectrochemistry (SEC) of a chiral binaphthalenylamine derivative of the N-butyl naphthalenediimide (NDIB-NH2) enantiomers were applied to measure UV–vis and ECD spectra of NDIB-NH2 radicals and dianion formed in the reduction and oxidation processes observed in cyclic voltammetry (CV). The CV curves and EPR spectroelectrochemistry enabled us to establish conditions at which a radical-anion [NDIB-NH2]̇.−, a dianion [NDIB-NH2]2−, and a radical-cation [NDIB-NH2]̇.+ are formed. The UV–vis spectra of radical-anion and dianion show the most significant changes in the 400–800 nm range. For the first time, an isosbestic point (455 nm) was found in ECD spectroelectrochemical measurements for the radical-cation [NDIB-NH2]̇.+ in equilibrium with the NDIB-NH2 neutral form. The TD-DFT CAM-B3LYP-D3/6-31G** calculations combined with the hybrid (explicit combined with implicit) solvation model fairly well reproduced the UV–vis and ECD SEC of neutral and redox forms of NDIB-NH2 but the ECD spectrum of [NDIB-NH2]̇.+ above 390 nm.

(2026-04-20)
Subject
Chemistry
Keyword

EPR, SEC, ECD, Isosbestic point, Cyclic voltammetry, TD-DFT, Hybrid solvation

Related Publication

Krzysztof Karoń, Joanna E. Rode, Dorota Kaczorek, Robert Kawęcki, Sandra Pluczyk-Małek, Mieczysław Łapkowski, Sławomir Ostrowski, Krzysztof Lyczko, Jan Cz. Dobrowolski, UV–Vis and ECD spectroelectrochemistry of atropisomeric naphthalenediimide derivative,Spectrochim. Acta A, 2023, 288, 122089 https://doi.org/10.1016/j.saa.2022.122089 doi: 10.1016/j.saa.2022.122089

CC BY - Creative Commons Attribution 4.0 CC BY - Creative Commons Attribution 4.0

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2023-SEC-ECD-SAA-SI.pdf
Adobe PDF - 3.1 MB - Apr 20, 2026 - 1 Download
MD5: fbbc714cc82f70778cf89b75f58ad0b5
License: CC BY - Creative Commons Attribution 4.0
Materiały uzupełniające publikacji Spectrochim. Acta A, 288(2023)122089.
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calculations-Restricted-Open-shell.zip
ZIP Archive - 91.7 MB - Apr 20, 2026 - 0 Downloads
MD5: 452e50bf09355f87b1ae80095dabb2d2
License: CC BY - Creative Commons Attribution 4.0
Output (*.out) and formatted checkpoint (*.fchk) files of quantum-chemical calculations performed at the CAM-B3LYP-D3/def2-TZVP/PCM(ACN) level within the Restricted Open Shell Approach (RO) of the NDIB–NH2 radical-anion and radical-cation. These data contains data of spin values spread over the studied radicals which were used to prepare Fig. 2c, Fig. 2d, Fig. 4, and data incorporated in Table 1. All calculations were performed using the Gaussian 09 package and the structures and orbitals were visualized using GaussView.
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calculations-UV-ECD-orbitals.zip
ZIP Archive - 287.7 MB - Apr 20, 2026 - 0 Downloads
MD5: 1dff5a1402cc0c608ea724d7b9b27900
License: CC BY - Creative Commons Attribution 4.0
Output (*.out) and formatted checkpoint (*.fchk) files of quantum-chemical calculations performed by using the time-dependent density functionals theory (TD-DFT) combined with CAM-B3LYP-D3 level and different solvation models. The calculations within the PCM solvation model were performer by using the def2-TZVP basis set. In the hybrid solvation (explicit combined with implicit) eleven explicit acetonitrile molecules formed the single shell surrounding the solute, and additionally, a continuous solvent model mimicked the next solvation spheres. In this approach the 6-31G** basis set was applied. These data contain the calculated UV and ECD spectra of all forms of NDIB–NH2 molecule under electric field: neutral, radical anion, dianion, and radical-cation. The data were used to prepare Figs. 3-5, Figs. S6-S8, and Tables 1 and S3. All calculations were performed using the Gaussian 09 package and the structures and orbitals were visualized using GaussView.
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experimetal-SEC-ECD-oxidation.zip
ZIP Archive - 414.0 KB - Apr 20, 2026 - 1 Download
MD5: c71d7f167c555a1dd76ba9320ad51489
License: CC BY - Creative Commons Attribution 4.0
Experimental UV–vis and ECD spectra of both enantiomers of chiral NDIB-NH2 registered upon oxidation process. Following electrode potentials were applied: 0mv (p0000mV files), 1000mV (p1000mV files), 1250mv (p1250mV files) and 1500mv (p1500mV files). The backgrounds were corrected using 0.2 M Bu4NPF6/ACN electrolyte solution recorded at the same conditions. The measurements were done in the same cell using a Jasco J-1500 ECD spectrometer and an Edaq ER466 potentiostat. The spectra were recorded in the 220–800 nm range, with a resolution of 0.2 nm, scanning speed of 200 nm/min, a bandwidth of 1 nm, three or more accumulated scans, room temperature, and concentrations depending on the range. These data were used to prepare Fig. 5 and Figs. S3, S4, S6.
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experimetal-SEC-ECD-reduction.zip
ZIP Archive - 728.5 KB - Apr 20, 2026 - 1 Download
MD5: 09aae0fc16571ae20e55e04b3f5cc85f
License: CC BY - Creative Commons Attribution 4.0
Experimental UV–vis and ECD spectra of both enantiomers of chiral NDIB-NH2 registered upon reductions process. The 0.13 mM NDIB-NH2 solutions in 0.2 M Bu4NPF6/ACN were used for the entire spectral range while a higher concentration (8.5 mM) for the range above 390 nm. Following electrode potentials were applied: 0mv (m0000mV files), -500mV (m0500mV files), -750mV (m0750mV files), -1000mV (m1000mV files), -1250mv (m1250mV files), -1500mv (m1500mV files) and -1750mV (m1750mV files). The backgrounds were corrected using 0.2 M Bu4NPF6/ACN electrolyte solution recorded at the same conditions. The measurements were done in the same cell using a Jasco J-1500 ECD spectrometer and an Edaq ER466 potentiostat. The spectra were recorded in the 220–800 nm range, with a resolution of 0.2 nm, scanning speed of 200 nm/min, a bandwidth of 1 nm, three or more accumulated scans, room temperature, and concentrations depending on the range. These data were used to prepare Figs. 5, 6 and Figs. S3-S6.
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