Notes - Synthesis of Some Derivatives of Phenothiasilin, A Silicon Analog of Thiaxanthene

Katashi Oita; Henry Gilman

doi:10.1021/jo01354a612

The Preparation of Some Derivatives of Phenoxasilin, a Silicon Analog of Xanthene

Journal of the American Chemical Society ◽

10.1021/ja01559a026 ◽

1957 ◽

Vol 79 (2) ◽

pp. 339-342 ◽

Cited By ~ 26

Author(s):

Katashi Oita ◽

Henry Gilman

Keyword(s):

Derivatives Of ◽

Silicon Analog

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Synthetic Routes to Novel Fluorogenic Pyronins and Silicon Analogs with Far-Red Spectral Properties and Enhanced Aqueous Stability

10.26434/chemrxiv.12055893 ◽

2020 ◽

Author(s):

Garance Dejouy ◽

Kévin RENAULT ◽

Ibai E. Valverde ◽

Anthony ROMIEU

Keyword(s):

Spectral Range ◽

Spectral Region ◽

Spectral Properties ◽

Activation Mechanism ◽

Spectral Features ◽

Primary Amino ◽

Meso Position ◽

Synthetic Routes ◽

Derivatives Of ◽

Silicon Analog

Fluorogenic detection of reactive (bio)analytes is often achieved with "smart" probes, whose activation mechanism causes the release of aniline-based fluorophores. Indeed, the protection-deprotection of their primary amino is the simplest way to induce dramatic and valuable changes in spectral features of the fluorogenic reporter. In this context, and due to their small size and intrinsic hydrophilicity, we focused on pyronin dyes and related heteroatom analogs (i.e., formal derivatives of 3-imino-3H-xanthen-6-amine and its silicon analog) for their use as optically tunable aniline-based fluorophores. To overcome some severe limitations associated with the use of such fluorogenic scaffolds (i.e., poor aqueous stability and spectral features only in the green-yellow spectral range), the synthesis of novel unsymmetrical derivatives of (Si)-pyronins bearing a single bulky tertiary aniline (i.e., N-methylindoline and julolidine) was explored and presented in this Article. This structural alteration has been found to be beneficial to dramatically lower electrophilicity of the meso-position and to reach attractive fluorescence properties within the far-red spectral region.

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Synthetic Routes to Novel Fluorogenic Pyronins and Silicon Analogs with Far-Red Spectral Properties and Enhanced Aqueous Stability

10.26434/chemrxiv.12055893.v1 ◽

2020 ◽

Author(s):

Garance Dejouy ◽

Kévin RENAULT ◽

Ibai E. Valverde ◽

Anthony ROMIEU

Keyword(s):

Spectral Range ◽

Spectral Region ◽

Spectral Properties ◽

Activation Mechanism ◽

Spectral Features ◽

Primary Amino ◽

Meso Position ◽

Synthetic Routes ◽

Derivatives Of ◽

Silicon Analog

Fluorogenic detection of reactive (bio)analytes is often achieved with "smart" probes, whose activation mechanism causes the release of aniline-based fluorophores. Indeed, the protection-deprotection of their primary amino is the simplest way to induce dramatic and valuable changes in spectral features of the fluorogenic reporter. In this context, and due to their small size and intrinsic hydrophilicity, we focused on pyronin dyes and related heteroatom analogs (i.e., formal derivatives of 3-imino-3H-xanthen-6-amine and its silicon analog) for their use as optically tunable aniline-based fluorophores. To overcome some severe limitations associated with the use of such fluorogenic scaffolds (i.e., poor aqueous stability and spectral features only in the green-yellow spectral range), the synthesis of novel unsymmetrical derivatives of (Si)-pyronins bearing a single bulky tertiary aniline (i.e., N-methylindoline and julolidine) was explored and presented in this Article. This structural alteration has been found to be beneficial to dramatically lower electrophilicity of the meso-position and to reach attractive fluorescence properties within the far-red spectral region.

Download Full-text