Effect of alkyl chains on luminescence properties with 3-hydroxy-2-naphthoate esters

Zhu, 2019, Organocatalytic atroposelective construction of axially chiral arylquinones, Nat. Commun., 10, 1, 10.1038/s41467-019-12269-4 Wang, 2012, New homochiral ferroelectric supramolecular networks of complexes constructed by chiral S-naproxen ligand, CrystEngComm, 14, 3802, 10.1039/c2ce25138h Yan, 2020, A fluorescent probe for Gallium(III) ions based on 2-hydroxy-1-naphthaldehyde and L-serine, Dyes Pigments, 175, 108190, 10.1016/j.dyepig.2020.108190 Zhan, 2020, Fluorescence response of anthracene modified D-pi-A heterocyclic chromophores containing nitrogen atom to mechanical force and acid vapor, Dyes Pigments, 173, 108002, 10.1016/j.dyepig.2019.108002 Zhao, 2020, Five naphthalene-amide-bridged Ni(ii) complexes: electrochemistry, bifunctional fluorescence responses, removal of contaminants and optimization by CVD, CrystEngComm, 22, 1330, 10.1039/C9CE01764J Bai, 2021, Circularly polarized luminescence from solvent-free chiral organic pi-liquids, Angew. Chem. Int. Ed., 60, 3745, 10.1002/anie.202013550 Dusold, 2021, pi-Extended diaza 7 helicenes by hybridization of naphthalene diimides and hexa-peri-hexabenzocoronenes, Chem. Eur. J., 27, 2332, 10.1002/chem.202003402 Hao, 2020, Modulation of solid-state optical properties of o-hydroxynaphthoic acids through formation of charge transfer cocrystals with TCNB, Cryst. Growth Des., 20, 7492, 10.1021/acs.cgd.0c01169 Kuznetsova, 2020, Coordination polymers based on highly emissive ligands: synthesis and functional properties, Materials, 13, 2699, 10.3390/ma13122699 Liu, 2020, Photochromic and photocontrolled luminescence properties of two metal-organic frameworks constructed from a naphthalene diimide derivative, Dyes Pigments, 172, 107856, 10.1016/j.dyepig.2019.107856 Apaydin, 2017, Electrochemical capture and release of CO2 in aqueous electrolytes using an organic semiconductor electrode, ACS Appl. Mater. Interf., 9, 12919, 10.1021/acsami.7b01875 Pu, 2011, Enantioselective fluorescent sensors: a tale of BINOL, Acc. Chem. Res., 45, 150, 10.1021/ar200048d Wu, 2019, New opportunities in synthetic macrocyclic arenes, Chem. Commun., 55, 1533, 10.1039/C8CC09374A Della Sala, 2020, Prismarenes: a new class of macrocyclic hosts obtained by templation in a thermodynamically controlled synthesis, J. Am. Chem. Soc., 142, 1752, 10.1021/jacs.9b12216 Yang, 2020, Naphthotubes: macrocyclic hosts with a biomimetic cavity feature, Acc. Chem. Res., 53, 198, 10.1021/acs.accounts.9b00415 Yang, 2020, Tiara[5]arenes: synthesis, solid-state conformational studies, host–guest properties, and application as nonporous adaptive crystals, Angew. Chem. Int. Ed., 59, 3994, 10.1002/anie.201913055 Pan, 2017, Regioselective synthesis of methylene-bridged naphthalene oligomers and their host–guest chemistry, J. Org. Chem., 82, 9570, 10.1021/acs.joc.7b01579 Gupta, 2019, Catalytic asymmetric epoxidation of aldehydes with two VANOL-derived chiral borate catalysts, Angew. Chem. Int. Ed., 58, 3361, 10.1002/anie.201809511 de Azambuja, 2020, Connecting remote C-H bond functionalization and decarboxylative coupling using simple amines, Nat. Chem., 12, 489, 10.1038/s41557-020-0428-1 Woods, 2020, Photocontrolled synthesis of n-type conjugated polymers, Angew. Chem. Int. Ed., 59, 6062, 10.1002/anie.201915819 Doswald, 2021, Preparation of functionalized carbon-coated cobalt nanoparticles with sulfonated arene derivatives, a study on surface functionalization and stability, Chem. Eur. J., 27, 4108, 10.1002/chem.202004631 Tang, 2015, Multi odd-even effects on cell parameters, melting points, and optical properties of chiral crystal solids based on S-naproxen, CrystEngComm, 17, 7258, 10.1039/C5CE01345C Yu, 2020, Identifying the naphthalene-based compound 3,5-dihydroxy 2-napthoic acid as a novel lead compound for designing lactate dehydrogenase-specific antibabesial drug, Front. Pharmacol., 10, 1663, 10.3389/fphar.2019.01663 Zhao, 2020, Recent advances of polymer acceptors for high-performance organic solar cells, J. Mater. Chem. C, 8, 28, 10.1039/C9TC05567C Souto, 2020, Electroactive organic building blocks for the chemical design of functional porous frameworks (MOFs and COFs) in electronics, Chem. Eur. J., 26, 10912, 10.1002/chem.202001211 Yang, 2019, Aromatic-diimide-based n-type conjugated polymers for all-polymer solar cell applications, Adv. Mater., 31 Nowak-Krol, 2019, Progress in the synthesis of perylene bisimide dyes, Org. Chem. Front., 6, 1272, 10.1039/C8QO01368C Insuasty, 2019, Recent advances in the core-annulation of naphthalene diimides, Chem. Eur. J., 25, 7058, 10.1002/chem.201806009 Genene, 2019, Recent advances in n-type polymers for all-polymer solar cells, Adv. Mater., 31, 10.1002/adma.201807275 Sheng, 2019, A naked-eye colorimetric sensor for chloroform, Chin. Chem. Lett., 30, 895, 10.1016/j.cclet.2019.01.027 Chen, 2017, A superior fluorescent sensor for Al3+ and UO22+ based on a Co(ii) metal–organic framework with exposed pyrimidyl Lewis base sites, J. Mater. Chem. A, 5, 13079, 10.1039/C7TA01546A Taheriha, 2016, Dimeric and polymeric mercury(II) complexes of 1-methyl-1,2,3,4-tetrazole-5-thiol: synthesis, crystal structure, spectroscopic characterization, and thermal analyses, J. Mol. Struct., 1107, 57, 10.1016/j.molstruc.2015.11.012 Wang, 2016, Microporous Cd(II) metal-organic framework as fluorescent sensor for nitroaromatic explosives at the sub-ppm level, J. Mol. Struct., 1107, 1, 10.1016/j.molstruc.2015.11.018 Zhao, 2022, Facile one-pot synthesis of a novel all-carbon stair containing dimerized pentalene core from alkyne, Chin. Chem. Lett., 33, 2047, 10.1016/j.cclet.2021.10.036 Choi, 2019, Synthesis and anti-endoplasmic reticulum stress activity of N-substituted-2-arylcarbonylhydrazinecarbothioamides, Med. Chem. Res., 28, 2142, 10.1007/s00044-019-02442-1 Park, 2016, Anti-diabetic effect of 3-hydroxy-2-naphthoic acid, an endoplasmic reticulum stress-reducing chemical chaperone, Eur. J. Pharmacol., 779, 157, 10.1016/j.ejphar.2016.03.023 Morrison, 2016, Synthesis of linear and angular aryl-morpholino-naphth-oxazines, their DNA-PK, PI3K, PDE3A and antiplatelet activity, Bioorg. Med. Chem. Lett., 26, 5534, 10.1016/j.bmcl.2016.10.003 Turek, 1993, Processing property relationships of a thermotropic copolyester .1. Effect of capillary die aspect ratio, Polymer, 34, 2750, 10.1016/0032-3861(93)90117-S Romo-Uribe, 2018, Synchrotron scattering and thermo-mechanical properties of high performance thermotropic polymer. A multi-scale analysis and structure-property correlation, Polymer, 153, 408, 10.1016/j.polymer.2018.08.038 Wagner, 2015, Hauser–Heck: efficient synthesis of γ-Aryl-β-ketoesters en route to substituted naphthalenes, Org. Lett., 17, 5670, 10.1021/acs.orglett.5b02952 Aluvila, 2010, Inhibitors of the mitochondrial citrate transport protein: validation of the role of substrate binding residues and discovery of the first purely competitive inhibitor, Mol. Pharmacol., 77, 26, 10.1124/mol.109.058750 Wang, 2008, Piperidinium 3-hydr-oxy-2-naphthoate, Acta Crystallogr Sect E Struct Rep Online, 64, o1753, 10.1107/S1600536808025567 Dai, 2020, 5-Fluorouracil cocrystals with lipophilic hydroxy-2-naphthoic acids: crystal structures, theoretical computations, and permeation studies, Cryst. Growth Des., 20, 923, 10.1021/acs.cgd.9b01310 Lou, 2011, Different hydrogen-bonded interactions in the cocrystals of nicotinamide with two aromatic acids, J. Chem. Crystallogr., 41, 1663, 10.1007/s10870-011-0154-z Jin, 2013, Eight salts constructed from 4-phenylthiazol-2-amine and carboxylic acid derivatives through combination of strong hydrogen bonding and weak noncovalent interactions, J. Mol. Struct., 1049, 132, 10.1016/j.molstruc.2013.06.040 Ghosh, 2011, Co-crystals of sulfamethazine with some carboxylic acids and amides: co-former assisted tautomerism in an active pharmaceutical ingredient and hydrogen bond competition study, Cryst. Growth Des., 11, 3489, 10.1021/cg200334m Jacobs, 2010, Inclusion compounds of hydroxynaphthoic acids: co-crystal vs. salt formation, CrystEngComm, 12, 3065, 10.1039/c004458j Xie, 2019, Structures, single-molecule magnets, and fluorescent properties of four dinuclear lanthanide complexes based on 4-azotriazolyl-3-hydroxy-2-naphthoic acid, Inorg. Chem., 58, 5914, 10.1021/acs.inorgchem.9b00260 Schmidt, 2005, Magnetic properties of two double-layer structures built from hydroxynaphthoic acids and manganese, Acta Crystallogr. Sect. C, 61, m361, 10.1107/S0108270105015659 Zhang, 2006, catena-Poly[[[bis(3-hydroxynaphthalene-2-carboxylato)zinc(II)]-[mu]-4,4′-bipyridine-[kappa]2N:N'] hemihydrate], Acta Crystallogr. Sect. E, 62, m2238, 10.1107/S1600536806029667 Deng, 2004, Diaquabis(3-hydroxynaphthalene-2-carboxylato-[kappa]O)zinc(II), Acta Crystallogr. Sect. E, 60, m1568, 10.1107/S1600536804023669 Phukan, 2013, A supramolecular assembly and complexes of zinc 2-hydoxy-3-naphthoate, RSC Adv., 3, 1151, 10.1039/C2RA22811D Zeng, 2013, Unusual method for phenolic hydroxyl bridged lanthanide CPs: syntheses, characterization, one and two photon luminescence, Dalton Trans., 42, 2052, 10.1039/C2DT32233A Palanisami, 2011, Synthesis, spectral characterization, and single crystal X-ray structures of a series of manganese-2,2′-bipyridine complexes derived from substituted aromatic carboxylic acids, Inorg. Chim. Acta, 365, 430, 10.1016/j.ica.2010.09.040 Zheng, 2001, Toward designed assembly of microporous coordination networks constructed from silver(I)−hexamethylenetetramine layers, Inorg. Chem., 40, 3562, 10.1021/ic001237z Phukan, 2014, 3-Hydroxynaphthalene-2-carboxylic acid supported grid-like structure of cadmium chloride coordination polymer with 1,3-bis(4-pyridyl)propane, J. Mol. Struct., 1076, 614, 10.1016/j.molstruc.2014.08.006 Wang, 2020, Four luminescent metal-organic chain compounds based on semi-rigid N-donor ligands and 3-hydroxy-2-naphthoic acid for recognition of Fe3+ and Cr2O72− ions, Polyhedron, 179, 10.1016/j.poly.2020.114383 Liu, 2020, A new acylhydrazine N'-(1,3 dimethylbutylene)-3-hydroxy-naphthohydrazide based fluorescent sensor for the detection of Ni2+, Dyes Pigments, 181, 10.1016/j.dyepig.2020.108582 Pirkwieser, 2018, Novel 3-hydroxy-2-naphthoate-based task-specific ionic liquids for an efficient extraction of heavy metals, Front. Chem., 6, 172, 10.3389/fchem.2018.00172 Chen, 2019, Syntheses, crystal structures and fluorescent properties of two metal-organic frameworks based on pamoic acid, J. Solid State Chem., 270, 335, 10.1016/j.jssc.2018.11.027 Sahoo, 2019, Synthesis and optical properties of copper(II) and nickel(II) complexes of a highly fluorescent morpholine-derivative, Polyhedron, 171, 559, 10.1016/j.poly.2019.07.044 Jin, 2005, Ethyl 3-hydroxy-2-naphthoate, Acta Crystallogr. Sect. E, 61, o275, 10.1107/S1600536805000176 Turner, 2017 G.M. Sheldrick, SADABS; University of Göttingen: Göttingen, Germany (1996 and 2003). Bruker, A.X.S., SAINT software reference manual; Madison: WI (1998). Sheldrick, 1997 Sheldrick, 2008, A short history of SHELX, Acta Crystallogr. Sect. A, 64, 112, 10.1107/S0108767307043930 Dolomanov, 2009, OLEX2: a complete structure solution, refinement and analysis program, J. Appl. Cryst., 42, 339, 10.1107/S0021889808042726 Spek, 2009, Structure validation in chemical crystallography, Acta Crystallogr. D Biol. Crystallogr., 65, 148, 10.1107/S090744490804362X Bonesi, 2002, Electronic spectroscopy of N- and C-substituted chlorocarbazoles in homogeneous media and in solid matrix, J. Lumin., 97, 83, 10.1016/S0022-2313(01)00240-X Tang, 2017, Tunable photoluminescent materials based on two phenylcarbazole-based dimers through the substituent groups, J. Lumin., 185, 1, 10.1016/j.jlumin.2016.12.023 Wang, 2017, Structural and luminescent properties of a series of Cd(II) pyridyl benzimidazole complexes that exhibit extended three-dimensional hydrogen bonded networks, J. Coord. Chem., 70, 1168, 10.1080/00958972.2017.1299143 Wang, 2018, Syntheses, crystal structures and luminescent properties of two salts with 2-((1H-imidazol-1-yl)methyl)-1H-benzimidazole, J. Mol. Struct., 1156, 156, 10.1016/j.molstruc.2017.11.099 Lü, 2018, Luminescent behaviors of salts based on 2–phenyl–1H–benzimidazole, J. Lumin., 199, 200, 10.1016/j.jlumin.2018.02.064 Spackman, 2002, Fingerprinting intermolecular interactions in molecular crystals, CrystEngComm, 4, 378, 10.1039/B203191B McKinnon, 2004, Novel tools for visualizing and exploring intermolecular interactions in molecular crystals, Acta Crystallogr. Sect. B, 60, 627, 10.1107/S0108768104020300 Arjun, 2020, Crystal structure, Hirshfeld surface analysis, DFT and molecular docking studies on benzohydrazide derivatives as potential inhibitors of prostate cancer, Chem. Data Coll., 26 Kala, 2017, Crystal structure and Hirshfeld surface analysis of(E)-2-(1-(2-phenylhydrazono)ethyl)naphtholen-1-ol, Chem. Data Coll., 7-8, 107 McKinnon, 2007, Towards quantitative analysis of intermolecular interactions with Hirshfeld surfaces, Chem. Commun., 3814, 10.1039/b704980c Rajarajeswari G, 2020, Crystal structure, quantum chemical and Hirshfeld surface analysis of N-ethyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide, Chem. Data Coll., 25 Manjunatha, 2020, Solid state and computational studies of ambroxol hydrochloride drug, Chem. Data Coll., 27