Electronic structure and second-order nonlinear optical properties of lemniscular [16]cycloparaphenylene compounds

Gong, Lijing; Ma, Cheng; Lin, Wan-Feng; Lv, Jinkai; Zhang, Xiangyu

doi:10.1039/d0ra01323d

Cited by 9 publications

(4 citation statements)

References 66 publications

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“…Several stereogenic motif bearing curvedp araphenylene (PP) moieties were recently synthesized by different groups independently. [34][35][36][37][38] Quite recently,T anaka and co-workersr eportedt he chiroptical properties in curved PP system linked to axially chiral ethynylbinaphthyla nd ethynylbiphenyls pacers. [38] On the contrary,t he corresponding CPL properties were elucidated only in two cases.…”

Section: Introductionmentioning

confidence: 99%

Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State

Sato

Hasegawa

Nojima

et al. 2020

Chemistry A European J

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Ac urveds tereogenic [6]paraphenylene ([6]PP), anchoring ac hiral binaphthyl scaffold at 7,7'-positions, was prepared and investigated for its properties as as olid-state circularly polarized luminescence (CPL) dye. X-ray analysis revealed ah elicallyt wisted structureo fP Pu nits induced by axial chiralityo fbinaphthyl framework. The curved [6]PP exhibits fluorescencei np owder and polymethyl methacrylate (PMMA) film as well as solution. As ignificant increase in quantum yield was observed for an on-fluid PMMA film owing the suppression of the molecular motion.T he g CPL valueso ft he dye in solution and as PMMA filmw ere almost the same (4.3-4.4 10 À3)a nd lager than that in powder.T D-DFT calculationsi nt he excited state suggest that the exciton can be delocalized into at wisted PP unit to produce al arger magnetic transition dipole moment.

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Section: Introductionmentioning

confidence: 99%

Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State

Sato

Hasegawa

Nojima

et al. 2020

Chemistry A European J

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“…[23] The SCPP [10] molecule with this topology adopts a conjoined shape, which gives rise to a p orbital overlap and reduces internal strain. [24] From these theoretical results, the frontier orbital information and the HOMO and LUMO profiles, as well as their energy levels, can be obtained (Figure 2). Geometrical optimization results indicate that SCPP [10] features C 2 symmetry and the torsion angles of 24.44-46.078 between adjacent para-phenylene units .…”

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confidence: 99%

A Highly Strained All‐Phenylene Conjoined Bismacrocycle

et al. 2021

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Herein, we report the precise synthesis of a 3D highly strained all-phenylene bismacrocycle, termed conjoined (1,4)[10]cycloparaphenylenophane (SCPP[10]). This structure consists of a twisted benzene ring which is bridged twice by phenylene units anchored in two para-positions. The conjoined structure of SCPP[10] was confirmed in real space at the atomic scale by scanning tunneling microscopy. Theoretical calculations indicate that this bismacrocycle has a very high strain energy of 110.59 kcal mol À1 and the largest interphenylene torsion angle of 46.078 caused by multiple repulsive interactions. Furthermore, a 1:2 host-guest complex of SCPP-[10] and [6,6]-phenyl-C 61 -butyric acid methyl ester was investigated, which represents the first peanut-shaped 1:2 host-guest complex based on bismacrocycles.

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“…The introduction of B/N atoms can effectively regulate the charge redistribution. At present, there have been reported on the nonlinear optical (NLO) based on PLY and CPP. – However, there is still a lack of research on the NLO of the supramolecular complexes based on PLY and CPP. The study aims to employ supramolecular complexes as a versatile platform for the control of inter- and intramolecular charge transfer (CT) processes in order to achieve the modulation of second-order NLO responses.…”

Section: Introductionmentioning

confidence: 99%

Density Functional Theory Studies of B/N-Doped Phenalenyl Nanorings with C₆₀ for Tuning Second-Order Nonlinear Optical Properties

Huang,

Gan,

Liu

et al. 2023

ACS Appl. Nano Mater.

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A series of triangular nanorings, denoted B n N 3−n -CPLY 3 (n = 0, 1, 2, and 3), are designed by incorporating boron-/nitrogen-doped phenalenyl (B/N-PLY) units into cycloparaphenylene. These nanorings exhibit appropriate cavity size and shape complementarity to encapsulate fullerene (C 60 ), resulting in the formation of supramolecular complexes termed B n N 3−n -CPLY 3 @C 60 (n = 0, 1, 2, 3). The geometric and electronic structures of nanorings and supramolecular complexes are investigated by density functional theory. Importantly, the self-assembly strategy effectively enhances the second-order nonlinear optical (NLO) response of the supramolecular complexes. The findings demonstrate that the first hyperpolarizabilities of B n N 3−n -CPLY 3 @C 60 (n = 0, 1, 2) are higher compared to that of B 3 -CPLY 3 @C 60 , which is attributed to the intra-and intermolecular charge transfer (CT) regulated by adjusting the amount of the B/N-PLY unit. By absorption spectrum analysis, the absorption peaks of B n N 3−n -CPLY 3 @C 60 (n = 0, 1, 2) are attributed to the host−guest interaction between B n N 3−n -CPLY 3 and C 60 . Furthermore, CT spectroscopy, main electron transition, and CT properties are studied to gain insights into the optical properties of B n N 3−n -CPLY 3 @C 60 . This work not only emphasizes the importance of the B/N-PLY unit in supramolecular complexes to improve NLO properties but also shows that the B n N 3−n -CPLY 3 @C 60 complexes are important materials for optoelectronic applications.

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Electronic structure and second-order nonlinear optical properties of lemniscular [16]cycloparaphenylene compounds

Abstract: The nonlinear optical property of the studied compounds were studied with the aid of the DFT calculations.

Cited by 9 publications

References 66 publications

Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State

Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State

A Highly Strained All‐Phenylene Conjoined Bismacrocycle

Density Functional Theory Studies of B/N-Doped Phenalenyl Nanorings with C₆₀ for Tuning Second-Order Nonlinear Optical Properties

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Electronic structure and second-order nonlinear optical properties of lemniscular [16]cycloparaphenylene compounds

Abstract: The nonlinear optical property of the studied compounds were studied with the aid of the DFT calculations.

Cited by 9 publications

References 66 publications

Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State

Circularly Polarized Luminescence of a Stereogenic Curved Paraphenylene Anchoring a Chiral Binaphthyl in Solution and Solid State

A Highly Strained All‐Phenylene Conjoined Bismacrocycle

Density Functional Theory Studies of B/N-Doped Phenalenyl Nanorings with C60 for Tuning Second-Order Nonlinear Optical Properties

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Density Functional Theory Studies of B/N-Doped Phenalenyl Nanorings with C₆₀ for Tuning Second-Order Nonlinear Optical Properties