Synthesis, Crystal Structures, Fluorescence and Quantum Chemical Investigations of some Multi-Substituted Quinoline Deri
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ORIGINAL ARTICLE
Synthesis, Crystal Structures, Fluorescence and Quantum Chemical Investigations of some Multi-Substituted Quinoline Derivatives Thi Hong Hai Le 1 & Thi Ngoc Vinh Nguyen 2 & Tuan Cuong Ngo 1 & Van Co Le 1 & Thi Yen Hang Bui 1 & Thi Da Tran 1 & Huu Dinh Nguyen 1 & Luc Van Meervelt 3 Received: 10 September 2020 / Accepted: 5 November 2020 # Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Starting from eugenol (4-allyl-2-methoxyphenol) three new quinoline derivatives, namely 5-bromo-7-(carboxymethoxy)-6-hydroxy-1methylquinolin-1-ium-3-sulfonate (Q2, C12H10BrNO7S), 5-amino-7-(carboxymethoxy)-6-hydroxyquinolin-1-ium-3-sulfonate (Q4, C11H10N2O7S) and 7-(carboxymethoxy)-5,6-dihydroxylquinolin-1-ium-3-sulfonate (Q6, C11H9NO8), have been synthesized and crystallised as dihydrate. The best planes through the quinoline ring and the carboxymethoxy substituent is 6.60 (14), 7.28 (6) and 4.73 (7)° for Q2, Q4 and Q6, respectively. The crystal packing of Q2 is characterised by O-H…O, π …π and Br …pyridine interactions. The two water molecules bridge three sulphate groups. Infinite chains of Q4 running in the direction [021] are formed by O/N-H …O hydrogen bonds at both ends of the molecule. Parallel chains interact by O/N-H…O hydrogen bonds and π…π and C=O…phenyl stacking. The -NH2 substituent bridges two sulphate groups, while the two water molecules bridge the other functional groups. The packing of Q6 consists of sheets of molecules interaction through O/N-H…O hydrogen bonds while the two water molecules bridge all function groups present. Parallel sheets interact through π…π and C=O…pyridine stacking. An aqueous solution of Q2 and its precursor 7-(carboxymethoxy)-6-hydroxyquinolin-1-ium-3-sulfonate (Q) exhibits fluorescence which is pH dependent. The fluorescence intensity of a 10 μM solution of Q containing Zn2+ reaches its maximum for a [Zn2+]:[Q] ratio of 1:1. The fluorescence properties of Q, Q2, Q4 and Q6 were further investigated by DFT calculation methods. Keywords Quinoline . Crystal structure . Fluorescence . DFT calculation
Introduction Among heterocyclic compounds, quinoline that has attracted enormous attention of chemists as well as pharmacists due to its indispensable role in medicinal chemistry. Many quinoline derivatives have been used as the key building component to Correspondence email: [email protected] and [email protected] * Thi Hong Hai Le [email protected] * Luc Van Meervelt [email protected] 1
Department of Chemistry, Hanoi National University of Education, 136 Xuan Thuy - Cau Giay, Hanoi, Vietnam
2
Department of Science, Hong Duc University, 565 Quang TrungTan Son, Thanh Hoa, Vietnam
3
Department of Chemistry, KU Leuven, Celestijnenlaan 200F, PO box 2404, 3001 Leuven (Heverlee), Belgium
synthesize antimalarials, antibiotics, antibacterial, antifungal, anti-inflammatory and antitumoral [1–4]. A number of substituted quinolines and their complexes are also well-known fluorescent compounds with high quantum yields and can be used
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