Azobenzenes tethered with crown ether display photoresponsive complexation with alkali and alkali earth metal ions, and have potential applications in ion-selective membranes, chemically-modified field effect transistors, and photo-switchable receptors. Figure 1 shows a few selected early examples of azobenzocrown ethers; azobenzene 1 bearing two crown ether units, azobenzocrown ether 2 with the direct connection to the azobenzene unit (at the parapositions) within the macrocycle, and one linked to the ortho-positions of azobenzene 3. Despite the advances in the applications, there are only limited synthetic methods available for the preparation of azobenzocrown ethers. Most of the methods currently used rely on reductive macrocyclization of the corresponding nitroarenes, which often provides the desired azobenzocrown ether 5 in low yield with a substantial amount of the undesired azoxycrown ethers 6 as a byproduct (Scheme 1). As a result, their structural variation is mostly confined to the modification of substituents on the aromatic ring of azobenzene 3. In addition, the azobenzenes incorporating crown ether unit at the meta-positions have not been reported despite the potential interest. A few years ago, we reported a new synthetic approach to azobenzene, starting from aryl halides and N-aryl hydrazides, via the Pd-catalyzed coupling followed by direct oxidation of the resultant N,N'-diaryl hydrazides. We anticipated that our methodology would translate well for the synthesis of azobenzocrown ethers. Herein we wish to present our investigation on the synthesis of azobenzocrown ethers 7 tethered with a polyether unit at the meta-positions (Scheme 2). The synthesis began with the preparation of bis(m-bromophenyl) ethers 10a-10d, readily accessed from m-bromophenol and polyether bis-tosylates. Cu(I)-catalyzed coupling reactions of 10a-10d with N-Boc hydrazine provided the