Homochiral Supramolecular Compounds Constructed from Amino Acid Derivatives: Syntheses, Structures, Chiroptical, and Photoluminescence Properties

Li, Xinfa; Liu, Tian‐Fu; Hu, Bing; Li, Guoliang; Zhang, Hui; Cao, Rong

doi:10.1021/cg100163g

Cited by 28 publications

(16 citation statements)

References 56 publications

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“…2 N-Alkylated amino acids discussed in this paper. Previously investigated molecules [5][6][7][8][9][10][11][12] have been identified by their CSD 4 refcodes. zwitterionic L-Leu.…”

Section: Resultsmentioning

confidence: 99%

“…Fig. 8 Crystal packing of (a) L-Ile : D-Ala (FITHIZ), 16 (b) N-methyl-Ltryptophan (WAJBIS), 6 (c) N-(2-pyrimidylmethyl)-L-alanine (QURSIG), 7 N α ,N ε ,N ε -tri(cyanoethyl)-L-lysine (VEQZIB), 8 and (e) L-proline (PROLIN). 10 Color coding as in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Special attention has been given to structures where neither the N-substituent nor the regular side chain participates in strong hydrogen bonds. There are only five such entries in the CSD: N-methylglycine (sarcosine, CSD refcode YIHHON), 5 N-methyl-L-tryptophan (WAJBIS), 6 which is a naturally occurring substance called abrine, N-(2-pyrimidylmethyl)-L-alanine (QURSIG), 7 N α ,N ε ,N ε -tri(cyanoethyl)-L-lysine (VEQZIB), 8 potential antimicrobial properties, and tritylglycine (LEFPUH), 9 see Fig. 2.…”

Section: Introductionmentioning

confidence: 99%

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Hydrogen bond architecture in crystal structures of N-alkylated hydrophobic amino acids

2014

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“…2 N-Alkylated amino acids discussed in this paper. Previously investigated molecules [5][6][7][8][9][10][11][12] have been identified by their CSD 4 refcodes. zwitterionic L-Leu.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Hydrogen bond architecture in crystal structures of N-alkylated hydrophobic amino acids

2014

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“…The Zn-N bond distances [Zn1-N2 (imino), 2.067(4) Å, Zn1-N3 ( pyridine), 2.066 (5) Å, 1a; Zn1-N1 (imino), 2.057(1) Å, Zn1-N2 ( pyridine), 2.055 (6) Å, 2a] and those of the Zn-Cl bonds [Zn1-Cl1 2.199(2) Å, Zn1-Cl2 2.207(2) Å, 1a; Zn1-Cl1 2.188(5) Å, Zn1-Cl2 2.200(7) Å, 2a] are typical. 33 The bond angles of N-Zn-N, Cl-Zn-Cl are 79.68 (17)°and 119.15(7)°in 1a, and 79.75 (1)°and 117.35(4)°in 2a, respectively. However, in 1b, the pyridine nitrogen appears to be bound strongly with the Hg II center [Hg1-N2 (pyridine) 2.294(1) Å, Hg1-N1 (imino), 2.442(1) Å].…”

Section: Synthesis and Crystal Structuresmentioning

confidence: 97%

Facile luminescent tuning of Zn^II/Hg^II complexes based on flexible, semi-rigid and rigid polydentate Schiff bases from blue to green to red: structural, photophysics, electrochemistry and theoretical calculations studies

et al. 2015

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The photophysical properties of Zn(II)/Hg(II) Schiff base complexes could be fine and predictably tuned over a wide range of wavelengths by changing the ligand structures. A new series of polydentate Schiff base-type ligands, N,N'-bis(2-pyridinylethylidene)R(3)-1,2-diamine (), which contain a flexible, semi-rigid or rigid group (R(3) = butyl, cyclohexane, tolyl and phenylene), has been designed and employed for synthetizing new mononuclear or binuclear trans Zn(II)/Hg(II) complexes with a general formula of [M()Cl2] ( = N,N'-bis(2-pyridinylethylidene)phenylene-1,2-diamine, M = Zn, ; M = Hg, ), [M()Cl2] ( = N,N'-bis(2-pyridinylethylidene)toluene-3,4-diamine, M = Zn, ; M = Hg, ), [M2()Cl4]·nCH2Cl2 ( = N,N'-bis(2-pyridinylmethylene)cyclohexane-1,2-diamine, M = Zn, n = 0, ; M = Hg, n = 1, ), [M2()Cl4]·nCH3OH ( = N,N'-bis(2-pyridinylethylidene)cyclohexane-1,2-diamine, M = Zn, n = 1, ; M = Hg, n = 0, ), [M2()Cl4] ( = N,N'-bis(3-methoxy-2-pyridinylmethylene)-cyclohexane-1,2-diamine, M = Zn, ; M = Hg, ), [M2()Cl4]·nCH3CN ( = N,N'-bis(3-methoxy-2-pyridinylmethylene)butane-1,4-diamine, M = Zn, n = 4, ; M = Hg, n = 0, ). All the ligands and complexes have been characterized by elemental analyses, IR spectra, and (1)H NMR spectra. Twelve structures of , , , , , and crystallized in three different conditions are further determined by single-crystal X-ray diffraction analyses. Their properties are fully characterized by UV-vis and fluorescence spectra both in solution and the solid state at room temperature. The luminescence color of these Zn(II)/Hg(II) Schiff base complexes could be tuned from blue to green to red (429-639 nm for , 434-627 nm for ) in solution by changing the ligand conjugated systems from flexibile () to semi-rigid () to rigid (). The spectra of the free Schiff bases are centered around 402-571 nm, which are perturbed upon the coordination to the Zn(II)/Hg(II) ion. Both the electrochemical data and TD-DFT calculations show that the HOMO-LUMO band gap from the ligand to the complex is reduced by complexation. Meanwhile, the emission efficiencies of Zn(II)-complexes are found to be strongly dependent on the Schiff-base ligands with quantum yields ranging from 14% to 25% for . However, the emission efficiencies dramatically decline in Hg(II)-complexes with quantum yields ranging from 4% to 19%, due to the heavy atom effect.

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“…Amino acids are naturally derived optically active reagents, which are useful as chiral auxiliaries in asymmetric organic synthesis. Various attempts have been made to utilize amino acids, not only for peptide synthesis, but also as key components in self‐assembled molecules to enhance biodegradability,34 gel formation,30, 31 and regulated chiral higher‐order structures based on hydrogen‐bonding ability and optical activity 35. Sanders and co‐workers have assembled helical nanotubes consisting of N , N ′‐dimethylnaphthalenediimide having pendant carboxy groups derived from amino acids, in which the tubular structure is stabilized by hydrogen bonding between the carboxy groups 36…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Formation of an Azobenzene‐Based CD‐Active Supramolecular Cyclic Dimer

Sogawa

Terada

et al. 2015

Chemistry A European J

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A series of new photo-responsive amino acid-derived azobenzenedicarboxylic acid derivatives (S)-1 a-e were synthesized. Compound (S)-1 a in the trans form exhibited no circular dichroism (CD) signal in DMF under ambient conditions, whereas intense Cotton effects were observed upon UV irradiation, indicating the formation of a chiral supramolecular structure in the cis form. The CD signals disappeared when trifluoroacetic acid (TFA) was added to the solution. The ester counterpart [(S)-1 a'] showed no CD signal. Hydrogen bonding between the carboxy groups seemed necessary for constructing the supramolecular structure. The kinetic studies of cis to trans isomerization of (S)-1 a demonstrated that the formation of a chiral supramolecule enhances the stability of the cis-azobenzene structure. The ESI mass spectrum of stilbenedicarboxylic acid (S)-4, an analogue of (S)-1 b, confirmed the formation of a dimer. A theoretical CD study revealed that (S)-1 a in the cis form should be present as a cyclic chiral dimer.

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Homochiral Supramolecular Compounds Constructed from Amino Acid Derivatives: Syntheses, Structures, Chiroptical, and Photoluminescence Properties

Cited by 28 publications

References 56 publications

Hydrogen bond architecture in crystal structures of N-alkylated hydrophobic amino acids

Hydrogen bond architecture in crystal structures of N-alkylated hydrophobic amino acids

Facile luminescent tuning of Zn^II/Hg^II complexes based on flexible, semi-rigid and rigid polydentate Schiff bases from blue to green to red: structural, photophysics, electrochemistry and theoretical calculations studies

Photoinduced Formation of an Azobenzene‐Based CD‐Active Supramolecular Cyclic Dimer

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Homochiral Supramolecular Compounds Constructed from Amino Acid Derivatives: Syntheses, Structures, Chiroptical, and Photoluminescence Properties

Cited by 28 publications

References 56 publications

Hydrogen bond architecture in crystal structures of N-alkylated hydrophobic amino acids

Hydrogen bond architecture in crystal structures of N-alkylated hydrophobic amino acids

Facile luminescent tuning of ZnII/HgII complexes based on flexible, semi-rigid and rigid polydentate Schiff bases from blue to green to red: structural, photophysics, electrochemistry and theoretical calculations studies

Photoinduced Formation of an Azobenzene‐Based CD‐Active Supramolecular Cyclic Dimer

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Facile luminescent tuning of Zn^II/Hg^II complexes based on flexible, semi-rigid and rigid polydentate Schiff bases from blue to green to red: structural, photophysics, electrochemistry and theoretical calculations studies