Synthesis of photocaged diamines and their application in photoinduced self-assembly

Tomas Barra, Lily Arrue, Esteban Urzúa, Lars Ratjen

Resultado de la investigación: Article

Resumen

The photochemical cleavage of covalent bonds is an important strategy in protection group chemistry, as well as for the triggering of chemical events posterior to the application of the physicochemical stimulus. Photocages allow the arresting and traceless liberation of a chemical entity, which can be broadly applied as a functional control element in materials chemistry and the life sciences in general. Among the best studied and most versatile light-sensitive protecting groups known to date rank the o-nitrobenzyl derivatives, entities which are easily introduced to amines, thiols, and alcohols. Their photolability relies on a phototautomerisation-induced cleavage mechanism, a phenomenon largely dependent on the substitution pattern of the aromatic ring in the o-nitrophenyl-moiety. Although well described and studied in detail for the protection of amino groups of different nature, the photocaging of aliphatic diamines has not been described in detail to date. Because of their interesting properties as synthons in supramolecular and polymer chemistry alike, we wish to describe the efficient photocaging of diamines with o-nitrobenzyl derivatives, their photocleavage behavior over time, as well as their application in a photoinduced templated self-assembly reaction towards cyclic imines.

Idioma originalEnglish
Número de artículoe3935
PublicaciónJournal of Physical Organic Chemistry
DOI
EstadoPublished - 1 ene 2019
Publicado de forma externa

Huella dactilar

Diamines
diamines
Self assembly
self assembly
chemistry
cleavage
synthesis
polymer chemistry
Derivatives
life sciences
Covalent bonds
Imines
covalent bonds
Sulfhydryl Compounds
thiols
stimuli
imines
Amines
amines
Polymers

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Citar esto

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Synthesis of photocaged diamines and their application in photoinduced self-assembly. / Barra, Tomas; Arrue, Lily; Urzúa, Esteban; Ratjen, Lars.

En: Journal of Physical Organic Chemistry, 01.01.2019.

Resultado de la investigación: Article

TY - JOUR

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AU - Arrue, Lily

AU - Urzúa, Esteban

AU - Ratjen, Lars

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