High Uptake of the Carcinogenic Pararosaniline Hydrochloride Dye from Water Using Carbazole-Containing Conjugated Copolymers Synthesized from a One-Pot Cyclopentannulation Reaction

Suchetha Shetty; Noorullah Baig; Rupa Bargakshatriya; Sumit Kumar Pramanik; Bassam Alameddine

doi:10.1021/acsami.3c05639

High Uptake of the Carcinogenic Pararosaniline Hydrochloride Dye from Water Using Carbazole-Containing Conjugated Copolymers Synthesized from a One-Pot Cyclopentannulation Reaction

ACS Appl Mater Interfaces. 2023 Jun 14;15(23):28149-28157. doi: 10.1021/acsami.3c05639. Epub 2023 May 31.

Authors

Suchetha Shetty^{1

2}, Noorullah Baig^{1

2}, Rupa Bargakshatriya³, Sumit Kumar Pramanik³, Bassam Alameddine^{1

2}

Affiliations

¹ Department of Mathematics and Natural Sciences, Gulf University for Science and Technology, 40006 Hawally, Kuwait.
² Functional Materials Group, Gulf University for Science and Technology, 40006 Hawally, Kuwait.
³ CSIR-Central Salt and Marine Chemicals Research Institute, Gijubhai Badheka Marg, Bhavnagar, Gujarat 364002, India.

PMID: 37257132
DOI: 10.1021/acsami.3c05639

Abstract

Three conjugated copolymers CAP1-3 were synthesized in one-step via a typical [3+2] cyclopentannulation reaction using a specially designed diethynyl carbazole synthon with various dibrominated polycondensed aromatic hydrocarbons (PAHs). The desired copolymers CAP1-3 were obtained in excellent yields, and their structures were confirmed by ¹H- and ¹³C- nuclear magnetic spectroscopy (NMR), whereas gel permeation chromatography revealed weight-average molar masses (M_w) up to 19.9 kDa with a polydispersity index (PDI) in the range of 2.2-2.6. Interestingly, CAP1-3 exhibits an outstanding capacity to adsorb the carcinogenic pararosaniline hydrochloride dye (Basic Red 9, BR9) from aqueous solutions. Isothermal adsorption studies were carried out following the linear models of Langmuir and Freundlich, divulging an adsorption capacity maximum (q_m) toward BR9 of 483.09 mg g^-1. Investigation of the dye uptake mechanism on CAP1-3 revealed a pseudo-second-order kinetic model for the target copolymer that showed the highest uptake capacity. Recyclability tests disclosed an excellent adsorption efficiency of BR 9 reaching 93% after six cycles.

Keywords: Conjugated Copolymers; Cyclopentannulation; Dye Adsorption; Environmental Remediation; Pararosaniline hydrochloride (Basic Red 9).