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Donor-Acceptor-Donor 1H-Benzo[d]imidazole Derivatives as Optical Waveguides.

ABSTRACT: A new series of donor-acceptor-donor (D-A-D) structures derived from arylethynyl 1H-benzo[d]imidazole was synthesized and processed into single crystals with the goal of testing such crystals' ability to act as optical waveguides. Some crystals displayed luminescence in the 550-600 nm range and optical waveguiding behavior with optical loss coefficients around 10^-2 dB/μm, which indicated a notable light transport. The crystalline structure, confirmed by X-ray diffraction, contains internal channels that are important for light propagation, as we previously reported. The combination of a 1D assembly, a single crystal structure, and notable light emission properties with low losses from self-absorption made 1H-benzo[d]imidazole derivatives appealing compounds for optical waveguide applications.

SUBMITTER: Tardio C

PROVIDER: S-EPMC10304989 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Donor-Acceptor-Donor 1H-Benzo[d]imidazole Derivatives as Optical Waveguides.

Tardío Carlos C Álvarez Conde Javier J Rodríguez Ana María AM Prieto Pilar P Hoz Antonio de la A Cabanillas-González Juan J Torres-Moya Iván I

Molecules (Basel, Switzerland) 20230608 12

A new series of donor-acceptor-donor (D-A-D) structures derived from arylethynyl 1H-benzo[d]imidazole was synthesized and processed into single crystals with the goal of testing such crystals' ability to act as optical waveguides. Some crystals displayed luminescence in the 550-600 nm range and optical waveguiding behavior with optical loss coefficients around 10-2 dB/μm, which indicated a notable light transport. The crystalline structure, confirmed by X-ray diffraction ...[more]

PMID: 37375189

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Project description:Octopolar D2-symmetric chromophores, based on the MPZnM supermolecular motif in which (porphinato)zinc(II) (PZn) and ruthenium(II) polypyridyl (M) structural units are connected via ethyne linkages, were synthesized. These structures take advantage of electron-rich meso-arylporphyrin or electron-poor meso-(perfluoroalkyl)porphyrin macrocycles, unsubstituted terpyridyl and 4'-pyrrolidinyl-2,2';6',2″-terpyridyl ligands, and modulation of metal(II) polypyridyl-to-(porphinato)zinc connectivity, to probe how electronic and geometric factors impact the measured hyperpolarizability. Transient absorption spectra obtained at early time delays (tdelay < 400 fs) demonstrate fast excited-state relaxation, and formation of a highly polarized T1 excited state; the T1 states of these chromophores display expansive, intense T1 → T n absorption manifolds that dominate the 800-1200 nm region of the NIR, long (μs) triplet-state lifetimes, and unusually large NIR excited absorptive extinction coefficients [ε(T1 → T n ) ∼ 105 M-1 cm-1]. Dynamic hyperpolarizability (βλ) values were determined from hyper-Rayleigh light scattering (HRS) measurements, carried out at multiple incident irradiation wavelengths spanning the 800-1500 nm spectral domain. The measured βHRS value (4600 ± 1200 × 10-30 esu) for one of these complexes, RuPZnRu, is the largest yet reported for any chromophore at a 1500 nm irradiation wavelength, highlighting that appropriate engineering of strong electronic coupling between multiple charge-transfer oscillators provides a critical design strategy to realize octopolar NLO chromophores exhibiting large βHRS values at telecom-relevant wavelengths. Generalized Thomas-Kuhn sum (TKS) rules were utilized to compute the effective excited-state-to-excited-state transition dipole moments from experimental linear-absorption spectra; these data were then utilized to compute hyperpolarizabilities as a function of frequency, that include two- and three-state contributions for both β zzz and β xzx tensor components to the RuPZnRu hyperpolarizability spectrum. This analysis predicts that the β zzz and β xzx tensor contributions to the RuPZnRu hyperpolarizability spectrum maximize near 1550 nm, in agreement with experimental data. The TKS analysis suggests that relative to analogous dipolar chromophores, octopolar supermolecules will be likely characterized by more intricate dependences of the measured hyperpolarizability upon irradiation wavelength due to the interactions among multiple different β tensor components.

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Donor-Acceptor-Donor 1H-Benzo[d]imidazole Derivatives as Optical Waveguides.

Publications

Donor-Acceptor-Donor 1<i>H</i>-Benzo[<i>d</i>]imidazole Derivatives as Optical Waveguides.

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