Synthesis and photochromism of 3‐indylfulgides

Li, Yunzheng; Wang, Huan‐Zhong; Zhu, Hesun; Wang, Fan

doi:10.1002/cjoc.19910090310

Cited by 6 publications

(5 citation statements)

References 2 publications

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“…Previously reported indolylfulgides substituted at the 3-position on the indole and having hydrogen at the bridging position were initially obtained in their E -form and also could not be converted to the C -form 23-25. For the first time, we obtained the C -form of such a fulgimide with a hydrogen at the bridging position.…”

Section: Resultsmentioning

confidence: 91%

“…Photochromic studies demonstrated that 6C can be converted to 6E ( E -form due to IUPAC priority rules), but the reverse reaction was not observed (Scheme ). Previously reported indolylfulgides substituted at the 3-position on the indole and having hydrogen at the bridging position were initially obtained in their E -form and also could not be converted to the C -form. − For the first time, we obtained the C -form of such a fulgimide with a hydrogen at the bridging position. We did not investigate the optical properties of 6 further as it was not photochromic.…”

Section: Resultsmentioning

confidence: 92%

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Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides

et al. 2009

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Three novel aqueous soluble fulgimides, trifluoromethyl carboxylic acid indolylfulgimide 4, dicarboxylic acid indolylfulgimide 5, and carboxylic acid indolylfulgimide 6, were synthesized. Both 4 and 5 can switch back and forth between open and closed forms upon illumination with specific wavelengths of light, while 6 can only switch from the closed form to the open form. In sodium phosphate buffer (pH 7.4) at 37 °C, an unusual hydrolysis of the trifluoromethyl group of the closed form of 4 resulted in 5 which has an additional carboxylic acid group. The closed form of 5 was further decarboxylated to generate 6 which was not photochromic. In buffer, the open form of 4 degraded 20% after 10 days while the closed form of 4 was converted to 5 rapidly. In buffer, both leeswj@fiu.edu. Supporting Information Available: 1 H and 13 C NMR spectra of compounds 4, 5 and 6. This material is available free of charge via the Internet at

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 92%

Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides

et al. 2009

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“…At this juncture, the wavelength of these transitions can be compared to that of an experimentally reported spirofused polycyclic aromatic compounds are found to exhibit UV-absorption in 332-335 nm range. [40] Other transitions involving canonical orbitals and the contribution of each transition towards the excited state in percentage have been included in Table 4. M1 and M2 show a difference in the range of n to π* and π to π* UV-visible transitions.…”

Section: Charge Transfer After Excitationmentioning

confidence: 99%

DFT Studies on the Molecular Structure, Regioisomerism, Ground and Excited state Charge Transfer Properties of Spiro‐heterocycles

Anumol¹,

Jose²,

Joy³

2022

ChemistrySelect

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The electronic structure, stereochemical aspects and charge transfer properties of the spiro compound (5S,8S) spiro‐{6‐phenyl‐1‐aza‐3‐oxa‐7‐thia‐bicyclo[3,3,0]‐octene‐8,3’(2’H)‐indol}‐2’‐one (spiro bicyclo adduct) synthesized using the multi‐component reaction via 1,3‐dipolar cycloaddition of isatin and thioproline with the dipolarophile phenylacetylene have been studied. The two lowest energy regio‐isomers of the spiro heterocycle formed from the stereospecific dipolar reaction have been analysed along with the electron‐withdrawing and releasing substituents using DFT method at the CAM‐B3LYP/6‐311++G(d,p) level of theory. The atomic charges and the stabilization energy due to the intramolecular charge delocalization process calculated using the natural orbitals at the different molecular sites reveal the different donor‐acceptor interactions occurring in the system. The intramolecular electronic transitions (specifically n to π* and π to π*) is found to occur from the localized donor end component to the acceptor end components in the multi‐component system. The hole produced by the ionization of the entities is found to migrate from the thioproline component to the phenyl acetylene part in a time scale of around 4 fs. The electron‐withdrawing and donating substituents on the spirobicyclo adduct have been proven to tune the excited and ground state charge transfer properties uniquely. The results can shed light on how multi‐component reactions can be directed to produce spiro adducts with versatile applications.

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“…The stretching vibrations of B-H bonds have the same characteristics of multiply peaks at 2600-2700 cm -1 with high intensity as para isomers. 17,18,27…”

Section: Ir Spectramentioning

confidence: 99%

“…This computational method has ever been used to optimize the structures of 10 and 11 vertexes closo-heteroboranes and the optimized geometries are in good agreement with the experimental parameters. [15][16][17][18] It was also successfully applied to compute 12 vertexes closo-heteroboranes and their halogeno derivatives. As shown in Table 1, the bond parameters of three molecules, 1-SB 11 H 11 , 1-SeB 11 H 11 , and 12-Cl-1-SB 11 H 10 , are consistent with those obtained from experimental structures.…”

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confidence: 99%

Structures, IR, NMR Spectra and Thermodynamics Properties of Halogenated Compounds X‐1‐ZB₁₁H₁₀ (ZO, S, Se; XF, Cl, Br): A DFT Study

Li¹

2010

Chin. J. Chem.

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The halogenated compounds of twelve-vertex closo-1-ZB 11 H 11 (Z＝O, S, Se; X＝F, Cl, Br) have unusual stability. The structures of halogenated isomers obtained by DFT method indicate that the halogen atoms are more likely to attack the meta vertexes. The chemical thermodynamic properties show that the halogenations are spontaneous and exothermic. The result that both the optimized and experimental cages of closo-thiaborane have not changed after chlorination indicates that the substitution of a chlorine atom for a hydrogen atom of closo-thiaborane happens at outer of the cage. The calculated electronic structures show that the three-dimensioned aromaticity of cage would like positive chlorine atoms to attack. The halogenations by elemental halogen in the presence of metal halides were proved to belong to the electrophilic substitutions and the mechanism was discussed in details. The suggested transition state interpreted the experiments. The thermal rearrangement which was supposed early according to experiments was verified by the thermodynamic properties of chlorination theoretically. The IR and 11 B/ 1 H NMR isotropic chemical shifts were calculated and compared with the experimental data to reconfirm the structures of chlorinated closo-thiaborane. Furthermore, the predictions on the halogenated closo-oxaborane and closo-selenaborane are significant for the syntheses.

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Synthesis and photochromism of 3‐indylfulgides

Cited by 6 publications

References 2 publications

Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides

Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides

DFT Studies on the Molecular Structure, Regioisomerism, Ground and Excited state Charge Transfer Properties of Spiro‐heterocycles

Structures, IR, NMR Spectra and Thermodynamics Properties of Halogenated Compounds X‐1‐ZB₁₁H₁₀ (ZO, S, Se; XF, Cl, Br): A DFT Study

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Synthesis and photochromism of 3‐indylfulgides

Cited by 6 publications

References 2 publications

Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides

Synthesis and Optical Properties of Aqueous Soluble Indolylfulgimides

DFT Studies on the Molecular Structure, Regioisomerism, Ground and Excited state Charge Transfer Properties of Spiro‐heterocycles

Structures, IR, NMR Spectra and Thermodynamics Properties of Halogenated Compounds X‐1‐ZB11H10 (ZO, S, Se; XF, Cl, Br): A DFT Study

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Structures, IR, NMR Spectra and Thermodynamics Properties of Halogenated Compounds X‐1‐ZB₁₁H₁₀ (ZO, S, Se; XF, Cl, Br): A DFT Study