Selective switching of multiple azobenzenes

Abstract

Multi-state photoswitchable compounds are highly attractive for application in data storage or multi-responsive materials. Herein, a trisazobenzene macrocycle is presented, which can be switched selectively into three individual states.

Tuning of Bistability, Thermal Stability of the Metastable States, and Application Prospects in the C3‐Symmetric Designs of Multiple Azo(hetero)arenes Systems

“…Such systems in principle, exhibit photoswitching over 2 n states, where n =2, 3, 4, etc., is the number of unsymmetrical azoarenes. Alternatively, macrocyclic ring strain can also dictate such phenomenon [4e] . The concepts of multistate photoswitching are quite advantageous in designing smart materials, optomechanics, and optoelectronic devices [12] .…”

Hierarchical Synthesis, Structure, and Photophysical Properties of Gallium‐ and Ruthenium‐Porphyrins with Axially Bonded Azo Ligands

“…Azobenzene derivatives have been developed as photoresponsive triggersi nm olecularm achines, [1] biological systems, [2] and many other areasi nwhich bistability is important. [3] In particular,t he switchable natureo ft he azo group facilitates control of molecular configuration, and this allowsadesiredf unctiont o be fine-tuned. [4] Finally,t he attachmento fm ulticomponent, switchable systems to as urface is highly desirable to form functional nanosystems.…”

Starazo triple switches – synthesis of unsymmetrical 1,3,5-tris(arylazo)benzenes

“…After the successful synthesis of (E)-N-(3-nitro-5-(phenyldiazenyl)phenyl)acetamide (8), the reduction of the nitro group was attempted. However, the literature-known procedure of using sodium hydrosulfide did not yield the desired (E)-N-(3amino-5-(phenyldiazenyl)phenyl)acetamide (9). Alternative reduction attempts, such as using Pd/C-catalyzed reduction by H 2 in different solvents, SnCl 2 , or iron under acidic conditions were not successful either.…”

“…Even subtle interactions, such as London dispersion in alkyl-substituted ABs, can have a significant influence on their isomerization properties [3,4]. Also, the incorporation of AB units into cyclic [5] or macrocyclic structures can control the switching, depending, i.a., on symmetry and ring strain [6][7][8][9]. By combining these approaches, half-lives can be tuned from milliseconds to years.…”