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Search for "donor–acceptor conjugate" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Perspectives on push–pull chromophores derived from click-type [2 + 2] cycloaddition–retroelectrocyclization reactions of electron-rich alkynes and electron-deficient alkenes

Michio Yamada

Beilstein J. Org. Chem. 2024, 20, 125–154, doi:10.3762/bjoc.20.13

physicochemical properties of the family of these compounds that have been investigated is provided to clarify their potential for future applications. Keywords: click chemistry; donor–acceptor conjugate; intramolecular charge transfer; photoluminescence; photoinduced electron transfer; Introduction Push–pull

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Graphical Abstract

Scheme 1: Pathway of the [2 + 2] CA–RE reaction of an electron-rich alkyne with TCNE or TCNQ. EDG = electron-...

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Scheme 2: Reaction pathway for DMA-appended acetylene and TCNEO.

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Scheme 3: Pathway of the [2 + 2] CA–RE reaction between 1 and DCFs.

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Scheme 4: Sequential double [2 + 2] CA–RE reactions between 1 and TCNE.

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Scheme 5: Divergent chemical transformation pathways of TCBD 6.

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Scheme 6: Synthesis of 12.

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Scheme 7: [2 + 2] CA–RE reaction of 1 with 14. TCE = 1,1,2,2-tetrachloroethane.

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Scheme 8: Autocatalytic model proposed by Nielsen et al.

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Scheme 9: Synthesis of anthracene-embedded TCBD compound 19.

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Scheme 10: Sequence of the [2 + 2] CA–RE reaction between dibenzo-fused cyclooctyne or cyclooctadiyne and TCNE...

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Scheme 11: [2 + 2] CA–RE reaction between the CPP derivatives and TCNE. THF = tetrahydrofuran.

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Scheme 12: [2 + 2] CA–RE reaction between ethynylfullerenes 31 and TCNE and subsequent thermal rearrangement.

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Scheme 13: Pathway of the [2 + 2] CA–RE reaction between TCNE and 34, followed by additional skeletal transfor...

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Scheme 14: Synthesis scheme for heterocycle 38 from the reaction between TCNE and 1 in water and a surfactant.

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Scheme 15: Synthesis scheme of the CDA product 41.

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Scheme 16: Synthesis of rotaxanes 44 and 46 via the [2 + 2] CA–RE reaction.

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Scheme 17: Synthesis of a Cu^I bisphenanthroline-based rotaxane 50.

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Figure 1: Structures of the chiral push–pull chromophores 51–56.

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Figure 2: Structures of the axially chiral TCBD 57 and DCNQ 58 bearing a C₆₀ core.

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Figure 3: Structures of the axially chiral SubPc–TCBD–aniline conjugates 59 and 60 and the subporphyrin–TCBD–...

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Figure 4: Structures of 63 and the TCBD 64.

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Figure 5: Structures of the fluorophore-containing TCBDs 65–67.

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Figure 6: Structures of the fluorophore-containing TCBDs 68–72.

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Figure 7: Structures of the urea-containing TCBDs 73–75.

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Figure 8: Structures of the fullerene–TCBD and DCNQ conjugates 76–79 and their reference compounds 80–83.

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Figure 9: Structures of the ZnPc–TCBD–aniline conjugates 84 and 85.

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Figure 10: Structures of the ZnP–PCBD and TCBD conjugates 86–88.

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Figure 11: Structures of the porphyrin-based donor–acceptor conjugates (89–104).

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Figure 12: Structures of the porphyrin–PTZ or DMA conjugates 105–112.

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Figure 13: Structures of the BODIPY–Acceptor–TPA or PTZ conjugates 113–116.

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Figure 14: Structures of the corrole–TCBD conjugates 117 and 118.

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Figure 15: Structure of the dendritic TCBD 119.

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Figure 16: Structures of the TCBDs 120–126.

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Figure 17: Structures of the precursor 127 and TCBDs 128–130.

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Figure 18: Structures of 131–134 utilized for BHJ OSCs.

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Review

Published 22 Jan 2024

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The Ugi four-component reaction as a concise modular synthetic tool for photo-induced electron transfer donor-anthraquinone dyads

Sarah Bay,
Gamall Makhloufi,
Christoph Janiak and
Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 1006–1016, doi:10.3762/bjoc.10.100

anthraquinone-substituted aldehyde together with acetic acid and tert-butyl isocyanide for rapidly assembling a donor–acceptor conjugate 1 displaying a photo-induced electron transfer leading to a charge-separated state with a lifetime of >2 ns (Figure 1), as elucidated by femtosecond transient absorption

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Figure 1: Phenothiazine–anthraquinone dyad 1, donor-only (2) and acceptor-only (3) models assembled by Ugi 4C...

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Scheme 1: Ugi 4CR synthesis of donor–anthraquinone dyads 8.

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Scheme 2: Ugi 4CR synthesis of donor-only reference systems 10.

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Figure 2: Molecular structure of S(O)-1 (left) (30% ellipsoids, except for the CH₃CH₂ end of the hexyl group,...

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Figure 3: Cyclic voltammogram of dyad 8c (recorded in CH₂Cl₂, T = 298 K, c (8c) = 0.1 mol·L⁻¹, Pt working ele...

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Figure 4: DFT-computed (B3LYP, 6-311G*) frontier molecular orbitals HOMO (bottom) and LUMO (top) of the pheno...

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Figure 5: Normalized absorption spectra of the phenothiazine–anthraquinone dyad 8c (recorded in CH₂Cl₂, c (8c...

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Figure 6: Absorption spectra of Do–anthraquinone dyads 8c (top) and 8e (bottom) with the corresponding refere...

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Figure 7: Normalized absorption and emission spectra of Ugi-donor compounds 2 and 10 (recorded in CH₂Cl₂, T =...

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Figure 8: Emission spectra of donor-only system 2 phenothiazine–anthraquinone dyads 8a,b (top), and the donor...

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Full Research Paper

Published 05 May 2014

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