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

ABSTRACT: 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 pK _a makes the azonium form unsuitable, the neutral versions of these compounds undergo trans-to-cis photoisomerization with blue-green light and exhibit slow (?_1/2 ? 10 min) thermal reversion and so may find applications under physiological conditions.

SUBMITTER: Martinez-Lopez D

PROVIDER: S-EPMC6964645 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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

Martínez-López David D Babalhavaeji Amirhossein A Sampedro Diego D Woolley G Andrew GA

Beilstein journal of organic chemistry 20191230

Aminoazobenzene derivatives with four <i>ortho</i> 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-<i>ortho</i>-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 compou ...[more]

PMID: 31976009

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