Carbazoles constitute an important class of alkaloids that exhibit a wide variety of biological and pharmacological activities and unique thermal and electric properties. Specifically, benzo[b]carbazoles display a broad range of activities including antitumor, anti-cancer, anti-inflammatory, antifungal, antiestrogenic, and kinase inhibitory activities. In addition, highly π-extended benzocarbazoles are widely used as building blocks for organic light-emitting diodes, semiconductors, polymers, and chemiluminescent and electroluminescent materials. Due to the highly useful nature of carbazole-based frameworks, a number of methods for their synthesis have been developed. However, these approaches include intramolecular cycloadditions of building blocks prepared through multistep operations, generating products with limited substitution patterns. Therefore, the development of efficient approaches to aryl-annulated carbazole derivatives with diverse substitution patterns from commercially available feedstock is highly desirable. Based on the significant potential of 2-nitrosyrenes as the building for the construction of diverse carbazoles, herein, we disclose an unprecedented Cu(I)-catalyzed reactions of 2-nitrocinnamaldehydes with two equivalents of benzyl cyanides in the presence of a mild base to provide a diverse array of tetracyclic benzo[b]-carbazoles, pentacyclic naphtho[2,1-b]- and dibenzo[a,h]carbazoles, and hexacyclic benzo[a]naphtho[1,2-h]carbazoles (Scheme 1). The reaction proceeds via a sequential Michael addition/ intramolecular addition of an enol intermediate into a nitro group followed by a series of transformations to set the penultimate 6π-electrocyclization and the final oxidative aromatization. Some of the carbazole derivatives showed a significant potential to be used as an environmentally sensitive fluorescence sensors for Cu2+ ions.