Four new monocationic biphenyl derivatives 4a-d were prepared through two sequential steps. The first step involved the preparation of biphenylcarbonitrile derivatives 3a-d via a Suzuki coupling reaction between bromobenzonitrile derivatives 1a, b and the appropriate substituted phenylboronic acids 2a-d. The second step involved the treatment of carbonitrile derivatives 3a-d with lithium bis-trimethylsilylamide, followed by de-protection step and subsequent hydrochloride salt formation. Whereby, DFT calculations revealed that compounds 3a and 4a have high chemical reactivity among all the newly synthesized compounds with lower band gaps of -4.513 and -3.361 ev, respectively. Additionally, a prediction study for the biological activities was performed via using PASS online software which displayed promising activities of monocationic biphenyl derivatives for the treatment of tumor regression in neurocells and anticoagulanting activities.