Development of value-added micropatterned porous materials from naturally abundant polymers, such as cellulose, are of growing interest. In this paper, regioselectively modified amphiphilic cellulose azide, 3-O- azidopropoxypoly(ethylene glycol)-2,6-di-O-thexyldimethylsilyl cellulose, with different degrees of substitution (DS) and degrees of polymerization (DP) of the poly(ethylene glycol) (PEG) side chain, was synthesized and employed in the formation of honeycomb-patterned films. With the variation of the DP and/or DS, the amphiphilicity of the polymer and the pore size of the formed films changed accordingly. It was found that amphiphilicity of the cellulose azide played a significant role in the formation of honeycomb films. Balanced amphiphilicity was of particular importance in the formation of uniform honeycomb films. Via the CuI-catalyzed alkyne-azide [2 + 3] cycloaddition reaction, fluorescent avidin and quantum dots were attached to the films. By means of confocal microscopy, it was confirmed that the functional azido group was preferentially allocated inside the pores. This provides a platform for the development of advanced honeycomb materials with site-specific functionalities, such as biosensors.
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