Oxidation‐State‐Dependent Photochemistry of Sulfur‐Bridged Anthracenes

Christensen, Peter R.; Patrick, Brian O.; Caron, Élise; Wolf, Michael O.

doi:10.1002/ange.201306236

Cited by 6 publications

(4 citation statements)

References 33 publications

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“…The photoluminescence properties of sulfur-bridged chromophores are highly dependent on the oxidation state of the sulfur bridge. 24,25 Compounds 2−4 exhibit different emission behavior in solution based on the oxidation state of the bridges (Table 1): the sulfones are emissive while the sulfides show only very weak emission. The quantum yields of (2−4)-SO 2 are lower than for 5−7 (0.01, 0.056, and 0.16 for n = 2, 3, and 4, respectively) and are not proportional to n. 52 The emission of all the compounds red-shifts as the solvent polarity increases (Figure S15).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Soluble Oligo- and Polythienyl Sulfides and Sulfones: Synthesis and Photophysics

Caron

Wolf

2017

Macromolecules

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Oligomers and soluble polymers incorporating conjugated α-oligothiophene units bridged by sulfide and sulfone groups are reported. The oligomers and polymers are characterized by solution 1 H NMR spectroscopy, differential scanning calorimetry, thermogravimetric analysis, cyclic voltammetry, gel permeation chromatography, and photophysical methods. The energies of the frontier orbitals, the physical properties, and the optical absorption and emission of these oligomers and polymers were found to be dependent on the oxidation state of the bridging sulfur.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Soluble Oligo- and Polythienyl Sulfides and Sulfones: Synthesis and Photophysics

Caron

Wolf

2017

Macromolecules

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“…Synthesis and Reagents : The synthesis, purification, and characterization of AnSO are reported elsewhere . Polymer host materials PBMA (avg.…”

Section: Methodsmentioning

confidence: 99%

“…9,9′‐Bis(anthracene)sulfoxide (AnSO) is a recently discovered molecule that shows photochemically controllable luminescence intensity . In the presence of UV light (300–425 nm), the weakly luminescent AnSO (photoluminescence quantum yield, Φ PL < 1%) rapidly forms the highly luminescent molecule 9,9′‐bianthryl (BA, Φ PL ≈ 80%) in quantitative yield ( Figure ).…”

Section: Introductionmentioning

confidence: 99%

Photopatterned Multidimensional Fluorescent Images

Christensen

Wolf

2016

Adv Funct Materials

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New methods that yield covert fluorescent images are of significant interest for applications in anti-counterfeit technology. Printing methods that offer access to spatially controlled fluorescence intensity are needed in order to accurately reproduce unique and complex images. Herein, the use of photoreactive inks containing 9,9′-bis(anthracene)sulfoxide (AnSO) to create complex images with spatially controlled fluorescence intensity is presented. Under UV irradiation, the SO-bridge between anthracene units in AnSO is extruded to yield the highly luminescent molecule 9,9′-bianthryl (BA) in quantitative yields. The irreversible formation of BA is leveraged to create multidimensional fluorescent security features that can be patterned using light and easily interpreted using the CCD camera of a mobile phone.

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“…Recently, introducing main‐group elements (such as B, N, S, Si, P, etc.) into OCM has become a powerful strategy for fine‐tuning photophysics, redox characteristics, molecular organizations, and optoelectronic functionalities of the OCMs [8–16] . Among the main‐group elements, phosphorus (P) element is a special member due to its rich and well‐defined chemistry, such as oxidation, borylation, alkylation, metal coordination, etc [11] .…”

Section: Introductionmentioning

confidence: 99%

Facile Route to Novel Diazaphosphinine‐Based Polycyclic Aromatic Hydrocarbons

Yang

Liu

et al. 2022

Angew Chem Int Ed

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Doping main-group elements has become a unique strategy to fine-tune optoelectronic properties of organic π-conjugated molecules. Herein, we report the first example of diazaphosphinine based polycyclic hydrocarbons (DP-PAHs) via facile synthetic protocols. Synthesis of diazaphosphinine heterocycles harnesses mild and efficient PÀ N chemistry. The heterocycles readily undergo photocyclizations by using only oxidants. The photocyclization protocol is applicable to the heterocycles with various P-centers. We successfully extended the protocols in extended DP-PAHs with 13fused aromatic rings. Further adjusting P-chemistry allows to efficiently fine-tune the singlet and triplet emission characteristics. More importantly, single-molecule white-light-emitting character was achieved via the balanced singlet and triplet emission of DP-PAH. Therefore, this work opens up new horizons in the area of organic π-conjugated materials.

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Oxidation‐State‐Dependent Photochemistry of Sulfur‐Bridged Anthracenes

Abstract: Was macht der Schwefel? Über die photochemische Reaktivität einschließlich mechanistischer Studien Schwefel‐verbrückter Anthracene wird berichtet. Der Oxidationszustand des verbrückenden Schwefels (SOn) bestimmt das Verhalten der Moleküle im angeregten Zustand (siehe Bild).

Cited by 6 publications

References 33 publications

Soluble Oligo- and Polythienyl Sulfides and Sulfones: Synthesis and Photophysics

Soluble Oligo- and Polythienyl Sulfides and Sulfones: Synthesis and Photophysics

Photopatterned Multidimensional Fluorescent Images

Facile Route to Novel Diazaphosphinine‐Based Polycyclic Aromatic Hydrocarbons

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