Acid/Base‐Triggered Switching of Circularly Polarized Luminescence and Electronic Circular Dichroism in Organic and Organometallic Helicenes

Saleh, Nidal; Moore, Barry D.; Srebro, Monika; Vanthuyne, Nicolas; Toupet, Loı̈c; Williams, J. A. Gareth; Roussel, Christian; Deol, Kirandeep K.; Muller, Gilles; Autschbach, Jochen; Crassous, Jeanne

doi:10.1002/chem.201405176

Cited by 176 publications

(123 citation statements)

References 55 publications

Supporting

Mentioning

119

Contrasting

Order By: Relevance

“…The precursor Dy(tta) 3 ·2H 2 O [53] (tta − = 2-thenoyltrifluoroacetonate anion) and the ligand 3-(2-pyridyl)-4-aza [6]-helicene [40,54] L were synthesized following previously reported methods. All other reagents were commercially available and used without further purification.…”

Section: Synthesis General Procedures and Materialsmentioning

confidence: 99%

See 1 more Smart Citation

Slow Magnetic Relaxation in Chiral Helicene-Based Coordination Complex of Dysprosium

et al. 2016

Self Cite

View full text Add to dashboard Cite

Abstract:The complex [Dy(L)(tta) 3 ] with L the chiral 3-(2-pyridyl)-4-aza[6]-helicene ligand (tta − = 2-thenoyltrifluoroaacetonate) has been synthesized in its racemic form and structurally and magnetically characterized. [Dy(L)(tta) 3 ] behaves as a single molecule magnet in its crystalline phase with the opening of a hysteresis loop at 0.50 K. These magnetic properties were interpreted with ab initio calculations.

show abstract

Section: Synthesis General Procedures and Materialsmentioning

confidence: 99%

“…Complex 1 was obtained by the coordination reaction of the chiral 3-(2-pyridyl)-4-aza [6]helicene [39,40] ligand (L) and tris(2-thenoyltrifluoroaacetonate)bis(aqueous)Dy III in CH 2 Cl 2 (Scheme 1). 1 crystallizes in the triclinic centrosymmetric space group P-1 ( Figures 1 and S1, Table S1).…”

Section: Structurementioning

confidence: 99%

Slow Magnetic Relaxation in Chiral Helicene-Based Coordination Complex of Dysprosium

et al. 2016

Self Cite

View full text Add to dashboard Cite

show abstract

“…This reactivity, initially considered rare, is receiving a remarkable attention due to applications in catalysis (with different processes promoted by Pd(II), 5 Rh(III), 6 and Ru(II) 7 ), organic synthesis, 8 and as advanced materials (e.g. chemosensors 9 and chiroptical switches 10 ) and anticancer agents. 11 In addition, a series of studies in the gas phase has envisaged further potential applications.…”

Section: A N U S C R I P Tmentioning

confidence: 99%

Platinum(II), palladium(II) and gold(III) adducts and cyclometalated derivatives of 6-methoxy-2,2′-bipyridine: A comparative study

Maidich

Cinellu

Cocco

et al. 2016

Journal of Organometallic Chemistry

View full text Add to dashboard Cite

“…[1][2][3][4][5] Thus, much affords have been made towards controlling and understanding chirality in chemical synthesis and material design. [1][2][3][4][5] Thus, much affords have been made towards controlling and understanding chirality in chemical synthesis and material design.…”

Section: Introductionmentioning

confidence: 99%

Photophysical properties of quinoxaline-fused [7]carbohelicene derivatives

Liu

Pan

et al. 2015

RSC Adv.

View full text Add to dashboard Cite

Helicene and its derivatives have received much attention as the candidates of organic photoelectronic material. Recently, novel quinoxaline-fused [7]carbohelicene derivatives exhibit unique structural and photophysical properties, especially in the crystal states. However, their structure-property relationships have not been fully understood from the micromechanism, which is also important to further improve their performance. Here, the electronic transition, electronic circular dichroism (CD), second-order nonlinear optical (NLO) response and charge transport properties of five quinoxaline-fused [7]carbohelicene derivatives have been investigated based on density functional theory calculations. The experimental UV-Vis/CD spectra of the studied compounds were well reproduced by our calculations. Thus, we can assign their electron transition properties and absolution configurations (ACs) with high confidence. It is found that CD bands of quinoxaline-fused [7]carbohelicene derivatives mainly originate from exciton coupling between quinoxaline, phenyl or 4-methoxyphenyl and [7]carbohelicene, which is in sharp contrast to [7]carbohelicene. More interestingly, these derivatives possess large first hyperpolarizability values. For example, the βHRS value of compound 6 is 32.96 × 10 −30 esu, which is about 190 times larger than that of the organic urea molecule. The bandwidth of valence band of compound 2 is comparable to that of conduction band and slightly larger than that of tris(8-hydroxyquinolinato)aluminium. This means that compound 2 is the potential candidate as ambipolar charge transport material. Please do not adjust marginsPlease do not adjust margins modulates the LUMO energy level. As a consequence, LUMO energy of compound 2 is much lower than that of compound 1 (Table S6), which leads to the smaller energy gap (Eg) for compound 2. Moreover, the main electron transitions characters are of charge transfer from quinoxaline to [7]carbohelicene and vice versa (Fig. 3). On the basis of above analysis, it is found that involvement of quinoxaline unit not only modulates the electron absorption wavelength but also alter the electron transition property. Compounds 3 and 4 also exhibit four absorption bands, which is similar to those of compound 2. In other words, the substituent effect of phenyl or 4-methoxyphenyl group on the UV-Vis spectra of compound 2 is not great. It is noted that some of the molecular orbitals involved in these transitions partially located on the phenyl or 4-methoxyphenyl group. Fig. 2Calculated UV-Vis (left) and CD (right) spectra in gas phase of 1, 2, 3 and 4 at the TDB3LYP/6-31+G(d) level of theory along with the experimental spectra (red dashed line).

show abstract

Acid/Base‐Triggered Switching of Circularly Polarized Luminescence and Electronic Circular Dichroism in Organic and Organometallic Helicenes

Cited by 176 publications

References 55 publications

Slow Magnetic Relaxation in Chiral Helicene-Based Coordination Complex of Dysprosium

Slow Magnetic Relaxation in Chiral Helicene-Based Coordination Complex of Dysprosium

Platinum(II), palladium(II) and gold(III) adducts and cyclometalated derivatives of 6-methoxy-2,2′-bipyridine: A comparative study

Photophysical properties of quinoxaline-fused [7]carbohelicene derivatives

Contact Info

Product

Resources

About