Synthesis and characterization of bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives

Beilstein Journal of Organic Chemistry

David Martínez-López¹  Diego Sampedro¹  Amirhossein Babalhavaeji²  G. Andrew Woolley² 

[1] Departamento de Química, Universidad de La Rioja, Centro de Investigación en Síntesis Química (CISQ), Madre de Dios, 53, 26006 Logroño, Spain;Department of Chemistry, University of Toronto, 80 St. George St., Toronto, M5S 3H6, Canada;

关键词: azobenzene;    azonium;    molecular switches;    ortho substitution;    photoisomerization;    photoswitch;    visible light;   

DOI  :  10.3762/bjoc.15.296

来源: DOAJ

【 摘 要 】

Aminoazobenzene derivatives with four ortho substituents with respect to the N–N double bond are a relatively unexplored class of azo compounds that show promise for use as photoswitches in biology. Tetra-ortho-methoxy-substituted aminoazobenzene compounds in particular can form azonium ions under physiological conditions and exhibit red-light photoswitching. Here, we report the synthesis and characterization of two bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives. These compounds form red-light-absorbing azonium ions, but only under very acidic conditions (pH < 1). While the low pKa makes the azonium form unsuitable, the neutral versions of these compounds undergo trans-to-cis photoisomerization with blue-green light and exhibit slow (τ1/2 ≈ 10 min) thermal reversion and so may find applications under physiological conditions.

【 授权许可】

Unknown