A TD-DFT/DFT study on the ESIPT and photophysical properties of symmetrical 2-hydroxybenzilidene1,3-diamines derivatives

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The geometries and relative stabilities of 15 tautomeric forms and the corresponding isomers of the studied molecules have been identified and their relative stabilities are investigated. The potential energy profiles and intrinsic reaction coordinates (IRC) calculations along the proton transfer coordinates both in the ground and in the excited state are monitored as well. The impact of the donating (OMe) and withdrawing (NO2) groups on the single and double proton transfers are investigated both in the gas phase and solution.

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Nội dung Text: A TD-DFT/DFT study on the ESIPT and photophysical properties of symmetrical 2-hydroxybenzilidene1,3-diamines derivatives

Cite this paper: Vietnam J. Chem., 2023, 61(5), 612-620 Research article DOI: 10.1002/vjch.202300108 A TD-DFT/DFT study on the ESIPT and photophysical properties of symmetrical 2-hydroxybenzilidene1,3-diamines derivatives Shaaban A. Elroby1*, Osman I. Osman1, Abdesslem Jedidi1, Walid I. Hassan1, Saadullah G. Aziz1, Rifaat Hilal2 1 Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, 21589, Saudi Arabia 2 Chemistry Department, Faculty of Science, University of Cairo, Egypt Submitted March 7, 2023; Revised May 15, 2023; Accepted June 5, 2023 Abstract Density functional theory (DFT) and Time dependent density functional theory (TD-DFT) methods are used to simulate the photoexcitation and emission of the symmetrical 2-hydroxybenzilidene1,3-diamine (HBDA) Schiff base and some of its derivatives in the gas phase and solution. Our aim here is to explore the details of Excited-State Intramolecular Proton Transfer (ESIPT) which underlies the activity of HBDA molecules as fluorescent probes. The structures of HBDA in S0 and the S1 states are optimized utilizing the DFT and TD-DFT methods, respectively. Geometric configurations, electronic spectra, frontier molecular orbitals, and potential energy surfaces have all been computed and analyzed for the purpose of interpreting the mechanism of ESIPT. The geometries and relative stabilities of 15 tautomeric forms and the corresponding isomers of the studied molecules have been identified and their relative stabilities are investigated. The potential energy profiles and intrinsic reaction coordinates (IRC) calculations along the proton transfer coordinates both in the ground and in the excited state are monitored as well. The impact of the donating (OMe) and withdrawing (NO2) groups on the single and double proton transfers are investigated both in the gas phase and solution. Keywords. Hydrogen bond, molecular switches, proton transfer, excited state intramolecular proton transfer (ESIPT), Schiff bases, DFT, TD-DFT. 1. INTRODUCTION one another have been well established as hydrogen donor and acceptor sites, respectively, for building Carbonyl compounds and primary amines are ESIPT-based compounds that serve as metal ions- condensed to produce Schiff bases, commonly specific probes.[24,25] referred to as imines. They are of great chemical and Through keto-enol tautomerisms, the capacity of biological significance because of their simple hydrogen donor and acceptor sites increases in their synthetic flexibility, ease of synthesis, and unique excited state and causes the ESIPT phenomena. imine (CN) group characteristic, which makes During the proton transfer in the excited state, which imines good chelating agents.[1] Additionally, it has results in dual emission with a significant Stokes' been noted that Schiff bases are frequently utilized shift, the keto-form is stable relative to its enol- as precursors to numerous compounds with form.[26] A proton is engaged in intramolecular biological and economic significance.[2–6] hydrogen bonding exchanges between two Commonly referred to as molecular switches,[7] electronegative centers during the ultrafast salicylidene aniline Schiff bases (SAS) are dynamic photoinduced transition known as ESIPT. In lighting systems that exhibit thermochromism, applications, the photochemical properties of photochromism, solvatochromism, and nonlinear compounds having two PT sites provide a new route optical (NLO) switching features[8-21] both in for full-color tunability. Widespread interest is solution and as solids. When stimulated by changes generated for two PT site compounds when the in temperature or light, SASs can experience keto- excited state intramolecular double proton transfer enol tautomerism.[22–23] This is true for both of their (ESIDPT) reaction occurs. Salicylaldehyde is a intramolecular H-bond-characterized cis and trans classic compound having a derivative called HBDA isomers. The probes with the characteristic OH Schiff base (figure 1). (phenolic) and N (imine) functional groups next to Salicylaldehyde Schiff base is a typical molecule 612 Wiley Online Library © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH
25728288, 2023, 5, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300108 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Shaaban A. Elroby et al. with the ESIPT reaction that contains HBDA Schiff fluorescent probes for the detection of metal ions. base (figure 1), which is a derivative of The structures of HBDA in S0 and the S1 states are salicylaldehyde.[28-31] Salicylideneanilines Schiff optimized utilizing DFT and TD-DFT methods, bases were the subject of earlier experimental work respectively. For interpreting the mechanism of that raised the question of whether or not these ESIPT process, the geometric configurations, compounds are fluorescent probes based on excited electronic spectra, and frontier molecular orbitals state intramolecular proton transfer.[32-33] (FMOs), have been computed and discussed. The In the current study, we investigate the geometrical and relative stabilities of tautomeric photochemistry and photoswitching properties of forms and the corresponding isomers of the studied symmetrical 2-hydroxybenzilidene1,3-diamines molecules have been presented in section one. The (HBDA) Schiff bases which have two identical effect of electron-donating (OMe) and withdrawing intramolecular hydrogen bonds. The HBDA (NO2) groups on single and double proton transfers molecules are investigated theoretically, aiming at are examined both in the gas phase and solution. We exploring the details of the occurrence of the ESIPT have selected these two groups due to the process in the HBDA molecules which act as availability of experimental data. Scheme 1: The suggested mechanism of ESIPT process for the studied molecule (HBDA) 2. COMPUTATIONAL DETAILS To investigate the transfer barrier and thermodynamic effect and reveal ESPIT Gaussian 09[34] was used for all calculations in this mechanisms, the PES of the S0 and S1 states were paper. For the DFT/TD-DFT approaches,[35,36] The determined. The lowest 20 singlet–singlet transitions B3LYP functional and 6-311++G** basis set were of some isomers of the HBDA molecules were used. The 6-311++G** basis set has been used in an computed to determine the excitation energies, effort to produce results that are more precise by maximum absorbance (λmax), oscillator strengths (f) utilizing a triple split valence basis set in addition to and absorption spectra using CAM-B3LYP/6- the polarization functions ((d,p) or (**)).[37-40] 311++G** level of theory.[44] Chemcraft[41] and Chemissian1.4 software packages are used for visualization of our results. 3. RESULTS AND DISCUSSION To demonstrate that the geometries actually correspond to global minima, which are supported 3.1. Tautomerism and relative energies by the absence of imaginary frequencies, vibrational frequencies of both S0 and S1 were computed. The Based on the relative locations of the two OH implicit solvent effect (acetonitrile) was discussed groups, we have investigated 15 tautomeric forms using the conductor-like polarizable continuum for HBDA, which are shown in Scheme 1S. The model (CPCM).[42,43] We have selected acetonitrile fifteen tautomeric forms of HBDA were fully as solvent due to the availability of experimental optimized using B3LYP/6-311++G** level theory in data. the gas phase and in acetonitrile as the solvent. © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 613
25728288, 2023, 5, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300108 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry A TD-DFT/DFT study on the ESIPT … Acetonitrile was selected because experimental data gas phase, the attachment of the NO2 group has are available in this solvent for the parent HBDA rendered the EE form more stable than the KK and compound. Two identical intramolecular H-bonds EK forms by 7.32 and 3.20 kcal/mol, respectively. make up HBDA’s symmetrical structure at the The X-ray study of 2-[(3,4-dimethylphenylimino) global minimum equilibrium geometry, providing methyl]-4-nitrophenol has indicated that it exists in two favorable locations for an intramolecular the Enol form in the solid state. In contrast, OMe proton-transfer process. Tautomeric structures group does not have any effect on the order of the studied in the present work (scheme 1) represent the stability of the tautomeric forms of the parent different structures resulting from single or double HBDA molecule; but it increases the stability of KK proton transfers (Enol (EE), Enol-Keto (EK) and form by 0.7 kcal/mol. Results obtained so far Keto-Keto (KK)) and free rotation about C-C and C- confirms that, the B3LYP/6-311++G** level of N bonds (cis and trans). The most stable tautomeric theory used in the present work, is capable of forms which are characterized by intramolecular capturing the relative stabilities and mean energy hydrogen bond are shown in Scheme 2S. The features of the tautomeric processes of the studied relative stabilities computed applying B3LYP/6- molecules. 311++G** level of theory for all conformers in scheme 1, in the gas phase and in solution, are 3.2. Geometric structures shown in Figure 1S and registered in table S1. From these results, the general order of the stability of In the present section, we will focus on the HBDA tautomeric forms is EE>EK>KK. As it can mechanism of the proton transfer processes in the be noticed from the relative energies, the relative HBDA symmetric molecule, which has two stabilizes of all total Keto (KK) forms with respect intramolecular hydrogen bonds. The general to its most stable Enol form are in the range of 4.19 mechanism of ESIPT of such molecular systems is to 4.15 kcal/mol. The relative stabilities of the six summarized in scheme 1. Upon photoexcitation, the Enol forms (3 forms EE and 3 forms of EK) are in stable Enol form gets excited to the first state (S1) range of ca. 0.1-2 kcal/mol. The relative energies of giving an unstable form that can undergo proton these forms, in the gas phase and in solution, transfer to produce a Keto form with an energy calculated using 6-311++G** basis set are lower than that of the excited Enol form. The excited negligible. In conclusion, the coexistence of the six Keto form may emit light through fluorescence and stable Enol forms of HBDA, is possible; i.e. in the return to the Keto ground state. The molecular ground state, the equilibrium structure of HBDA is a planarity in Schiff bases is connected to statistical weighed mixture of these six enol forms. thermochromic and photochromic capabilities, The experimental and theoretical UV spectra according to Mavridis et al.[9] confirm this conclusion; which will be discussed in The fact that all of the structures depicted in the UV-calculation section. These findings are scheme 2S are fully optimized in both the ground consistent with earlier theoretical and experimental and excited states, as well as the existence of a research on HBDA,[45] which suggests that the single, unique imaginary frequency that corresponds molecule’s ground state is an enol form. The three to a transition state, demonstrate that they all map to tautomeric forms EE, EK, and KK, which are the minima on the potential energy surfaces. The solvent most stable, will be the subject of the following effects were taken into consideration using the section. polarizable continuum model (CPCM). The effect of NO2 and OMe substituents as electron withdrawing and donating groups, respectively, on the tautomeric process as well as on the mechanism of the proton transfer in ground (S0) and excited (S1) states are discussed. Careful examination of both the total electronic and relative energies are compiled in table S2; which were calculated in solution, using B3LYP/6-311++G** level of theory. They show that the NO2 group stabilizes the KE and KK forms over the total Enol form (EE) by 3.556 and 0.797 kcal/mol, Figure 1: The atom numbering of the stable cis-enol respectively. The energy difference between EE and form of the HBDA molecule KK is very small, which could be indicative of the coexistence of these two tautomeric forms. In the In general, the geometrical structure of all the © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 614
25728288, 2023, 5, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300108 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Shaaban A. Elroby et al. studied molecules is symmetrical in S0 and found that the O32-H47 bond length of EE-cis, EE- asymmetrical in S1 as illustrated in table 1. Thus, it NO2, and EE-OMe in the S0 state were 0.997, 1.005, can be verified that the ESIDPT reaction and 0.996 Å, respectively; while in the S1 state, it mechanisms of the studied molecules consist of two decreased to 0.974 and 0.979 Å in EE-cis and EE- steps. The information about the major bond lengths NO2 respectively but increased in EE-OMe to 1.00 and bond angles of each structure in the S0 and S1 Å (table 2). During photoexcitation (S0-S1), the H12- states is listed in table 1. From these results, we N1 bond lengths in EE-cis, EE-NO2, and EE-OMe Table 1: Total and Relative energies (kcal/mol) in S0 and S1 states, for all the tautomeric forms with OMe and NO2 substituents based on the B3LYP-D3/6-311++G** level in acetonitrile as solvent NO2 OMe H EE KK EK EE KK EK EE KK EK S0 / in solution G/au -1440.8908 -1440.8909 -1440.8927 -1260.8004 -1260.7956 -1260.7980 -1031.7467 -1031.7408 -1031.7438 ΔGRe, kcal/mol 0.063 0.000 1.130 0.000 3.012 1.506 0.000 3.702 1.820 E-ZPE/au -1440.8323 -1440.8324 -1440.8331 -1261.7434 -1261.7370 -1261.7405 -1031.6967 -1031.6898 -1031.6935 ΔEZPE, kcal/mol 0.063 0.000 0.439 0.000 4.016 1.820 0.000 4.330 2.008 Dipole/Deby 1.76 7.39 6.603 8.63 13.64 11.342 6.84 11.49 6.1955 Ee/au -1441.1494 -1441.1450 -1441.1507 -1261.1206 -1261.1148 -1261.1179 -1032.0099 -1032.0033 -1032.0069 ΔE, kcal/mol 2.761 0.000 3.558 0.000 3.639 1.684 0.000 4.141 1.912 S1 / in solution Dipole/Deby 0.552 7.67 6.8895 10.43 14.2407 12.6188 9.3903 12.2955 10.1011 -1441.1316 -1441.1506 -1441.1450 -1261.1095 -1261.1061 -1261.1105 -1031.9428 -1031.9966 -1031.9993 Ee -1441.0294 -1441.0489 -1441.0472 -1261.0065 -1261.0264 -1261.0257 -1031.8806 -1031.9024 -1031.9046 Eex -0.1200 -0.096 -0.1035 -0.1141 -0.0884 -0.0922 -0.1293 -0.1009 -0.1023 λem/nm 380 448 440 399 514 494 358 455 445 Table 2: Some selected optimized parameters (bond lengths in Å and angles in deg.) of different substituents of the studied isomers in the S0 and S1 states using B3LYP/6-311++G** level of theory Conformer N8-H47 or substituent O32-H47 O29-H48 C13-O32 C25-O29 C12-C10 C20-C11 N9-H48 C10-N8 C11-N9 O-H s H EE 1.348 0.997 1.451 1.289 1.720 KK 1.260 1.393 1.333 1.684 EK 1.309 1.451 1.327 1.260 NO2 1.331 1.286 EE (1.328) 1.005 1.455 (1.286) 1.684 S0 KK 1.26 1.422 1.316 1.752 EK OMe EE 1.352 0.996 1.451 1.29 1.725 KK 1.271 1.398 1.331 1.74 EK H EE 1.365 0.974 1.409 1.393 1.943 1.347 0.996 1.450 1.290 1.726 KK 1.270 1.442 1.336 1.836 1.276 1.406 1.329 1.733 EE 1.352 .979 1.425 1.36 1.855 1.330 0.998 1.449 1.29 1.719 S1 NO2 KK 1.254 1.432 1.343 1.876 1.260 1.413 1.319 1.756 OMe EE 1.355 1.00 1.448 1.302 1.69 1.256 1.432 1.312 1.319 KK 1.294 1.467 1.360 1.72 © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 615
25728288, 2023, 5, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300108 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry A TD-DFT/DFT study on the ESIPT … elongate from 1.720, 1.684 and 1.725 Å to 1.943, The potential energy profiles for the proton 1.725 and 1.855 Å, respectively, whereas the H9-N1 transfer processes are illustrated and displayed in bond lengths shorten to 1.718, 1.69 and 1.49 Å, figure 2. For the parent HBDA, the first PT process respectively. From these values, it can be concluded takes the structure from the EE to the EK form that the hydrogen bonds O1-H9···N2 and O2- through a low laying (6.588 kcal/mol) transition H12···N1 are enhanced in the S1 state of EE-OMe state. The EK form seems to be a stable intermediate only. The O1-H9...N2 and O2-H12…N1 bond which is transformed through the second PT process angles increase in EE-OMe and decrease in EE-cis to the KK form through a barrier of 17.3 kcal/mol. and EE- NO2 molecules. The O1-H9...N2 bond These two PT processes seem to be energetically angle is 147o for EE-OMe in S0 and 149.3o and and kinetically visible; yet thermodynamically are 153.4o in S1. In contrast, The O1-H9...N2 angle is not favorable (H# = +4.14 kcal/mol). Substitution 148o for EE-cis in S0 and 147.6o and 142.3o in S1. In by the electron donating Methoxy group slightly the case of EE-NO2, the O1-H9...N2 decreases in S1 enhances the barrier of the EE-EK PT process and by 6o but by only 2o in S0. The changes in bond markedly lowers the EK-KK barrier. This would lengths and bond angles upon photoexcitation kinetically facilitate the DPT process, yet it is still indicate that the hydrogen bond is more stable in the thermodynamically not favorable. Substitution by S1 state of EE-OMe. Additionally, the presence of the electron withdrawing NO2 group, lowers the two the electron-donating substituent adjusts the barriers of the DPT process considerably and places the EK structure as a global minimum. Moreover, redistribution of electron density and interacts with the NO2 substitution makes the DPT process both the ESIPT and ESICT phenomena. kinetically and thermodynamically favorable. Figure 2: Energy profiles of the proton transfer in ground state of HBD and its substituents (total energy (au) and Barrier energy (kcal/mol) 3.3. Optical properties crucial. To excite an electron from its ground state to an excited state, it must not only be given a photon When establishing whether molecular excitation with the appropriate amount of energy, but also have takes place, the change in the dipole orientation is its electric field aligned with the transition dipole. © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 616
25728288, 2023, 5, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300108 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry Shaaban A. Elroby et al. An electron is promoted to an excited state when a transition as shown in table 3. This signifies that the photon of light strikes it; this process is known as electron density shifted from the N and O atoms to absorption. benzene rings. The two other peaks, correspond, on In the present work, different DFT functionals the other hand, to 𝜋-𝜋* transition and show electron have been applied for the TD-DFT excited state density transfer between benzene rings. study of the parent HBDA molecule. It is utilized The substantially Stokes-shifted emission in our because the CAM-B3LYP functional generates a system was thought to be caused by the proton- spectrum that, in terms of band location and absolute transferred tautomeric form. Additionally, in order intensity, agrees quite well with the experimental to further investigate the phenomena, theoretical spectrum that was observed. TD-DFT calculations calculations for HBDA in the ground and excited showed the six lowest - energy excited states. Those states utilizing the DFT/TD-DFT/B3LYP/6- with an excitation energy below 4.96 eV (above 250 311++G** levels of theory, respectively, have been nm) and an oscillator strength larger than 0.01 were made. The calculated absorption spectral peaks considered. By performing TD-DFT calculations on displayed a significant connection with the observed the four most stable isomers of HBDA in solution, results, indicating that the theory was successful in absorption and fluorescence maxima are estimated predicting the origin of the experimental as vertical S0-S1 excitation and vertical S1-S0 observations. emission energies, respectively. The absorption and fluorescence maxima were obtained at the same 4. CONCLUSION level of theory based on optimized geometries utilizing B3LYP-PCM/6-311++G** level of theory In the present study, DFT and TD-DFT calculations in conjunction with a state-specific PCM description were used to explore the reasons underlying the of the acetonitrile. All Enol tautomeric isomers EE utility of HBDA and its derivatives as fluorescent and EK have non-planar structures in the S0 state, probes. The relative stabilities of the different with no imaginary frequency. In contrast, KK forms tautomeric and isomeric forms of HBDA are are planar. Table 3 displays the calculated discussed in detail. Furthermore, the effect of absorption spectra and natural transition orbitals for substitution by NO2 and OMe on the transfer process the most stable tautomeric structures in acetonitrile. of proton, both in ground and excited states, were The results shown in table 3 indicate that the enol explored. Assessment of different DFT functionals is and keto forms of the studied molecule give three carried out and the Cam-B3LYP method was intense transitions (0.10 < f < 0.90) in the range of selected because it can reproduce the spectrum of 230 - 450 nm. The maximum wave length transition HBDA in extremely good agreement with the is the most intense and is dominated by a HOMO- experimental one. The origin of the observed LUMO character; whereas, the second most intense absorption and emission transitions were identified transition shows a strong HOMO-1 to LUMO and the underlaying corresponding tautomeric contribution. In comparison to its analog for the enol structure are inferred. form, the first absorption band of the keto forms (KK and EK) is consistently red-shifted by about 50 Acknowledgement. The authors extend their nm. According to the TD-DFT calculations, each appreciation to the Deanship for Research & isomer has three peaks with a strong oscillator. Innovation, Ministry of Education in Saudi Arabia We discovered that the estimated wave lengths for funding this research work through the project for the absorption maxima are in excellent number “G: 391-130-1443” and King Abdulaziz agreement with the corresponding experimental University, DSR, Jeddah, Saudi Arabia. values for all enol structures.[1] The calculated absorption peak for the enol form at ~347 nm REFERENCES originate from the HOMO→LUMO+1 transition with oscillator strength of 0.7039 which corresponds 1. C. M. Metzler, A. Cahill, D. E. Metzler, Equilibriums very well to the experimental value (347 nm). The and absorption spectra of Schiff bases, J. Am. Chem. other two peaks at ~306 nm and 273 nm seem to Soc., 1980, 102, 6075-6082. 2. A. Kajal, S. Bala, S. Kamboj, N. Sharma, V. Saini, originate from the HOMO-3→LUMO transition, Schiff bases: A versatile pharmacophore, J. Catal., with weak oscillator strengths ranging between 0.20 2013, Article ID 893512, 14 pages. to 0.10. 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25728288, 2023, 5, Downloaded from https://onlinelibrary.wiley.com/doi/10.1002/vjch.202300108 by Readcube (Labtiva Inc.), Wiley Online Library on [01/05/2024]. See the Terms and Conditions (https://onlinelibrary.wiley.com/terms-and-conditions) on Wiley Online Library for rules of use; OA articles are governed by the applicable Creative Commons License Vietnam Journal of Chemistry A TD-DFT/DFT study on the ESIPT … Table 3: Electronic absorption energy (nm/eV), corresponding oscillator strengths, assignments, and coefficients of the studied tautomers of parent compound obtained by using TD-DFT/CAM-B3LYP/6-311++G** level of theory in acetonitrile Compound (λ)em (λ)abs f MO (λ)exp Hole particle EE-trans 440 347 0.834 H → L+1 362 306 0.220 H-3 → L 347 273 0.366 H-4 → L 273 239 0.110 H-3 → L+2 232 EE-cis-1 354 0.644 H → L+1 340 0.196 H→L 307 0.082 H-3 → L EE-cis 351 344 0.900 n-𝜋* H → L+1 308 0.256 𝜋-𝜋* H-3 → L+1 271 0.527 𝜋-𝜋* H → L+1 KK-cis-1 460 449 0.663 H→L 406 0.206 H-1 → L+1 362 0.000 H-3 → L EK-cis 443 0.607 H→L 347 0.479 H-2 → L+1 327 0.320 H-2 → L © 2023 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 618
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