Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9-Diethylfluorene (Part I)

Overview

Journal ChemistryOpen

Specialty Chemistry

Date 2020 Dec 11

PMID 33304735

Citations 4

Authors

Pierre Seidel

Monika Mazik

Affiliations

Soon will be listed here.

Abstract

A series of new 9,9-diethylfluorenes consisting of three side-arms each bearing a heterocyclic, bis(carboxymethyl)amino, bis(carbamoylmethyl)amino, bis(ethoxycarbonylmethyl)amino or an amino group were prepared on the basis of 2,4,7-tris(bromomethyl)-9,9-diethylfluorene. Imidazolyl, benzimidazolyl, pyrazolyl, pyrrolyl, 1,3-dioxoisoindolyl and pyridinium groups were taken into account as heterocyclic units, attached to the aromatic skeleton via -CH-, -CHNHCH- or -CHN=CH- linkers. In addition to the seventeen 2,4,7-trisubstituted 9,9-diethylfluorenes, two macrocyclic compounds were prepared on the basis of 2,7-bis(aminomethyl)-9,9-diethylfluorene. The excellent yield of the macrocyclization reaction is worth a special mention. Both the acyclic and the macrocyclic fluorene-based compounds have, among other things, the potential to act as artificial receptors for different substrates in analogy to the known receptors consisting of a benzene or biphenyl core.

Citing Articles

Crystal structure and Hirshfeld surface analysis of 4,4'-di-meth-oxy-biphenyl-3,3',5,5'-tetra-carb-oxy-lic acid dihydrate.

Hanauer T, Seichter W, Mazik M Acta Crystallogr E Crystallogr Commun. 2024; 80(Pt 4):413-417.

PMID: 38584732 PMC: 10993599. DOI: 10.1107/S2056989024002305.

Cycloalkyl Groups as Building Blocks of Artificial Carbohydrate Receptors: Studies with Macrocycles Bearing Flexible Side-Arms.

Leibiger B, Stapf M, Mazik M Molecules. 2022; 27(21).

PMID: 36364458 PMC: 9654292. DOI: 10.3390/molecules27217630.

Crystal structure of 9,9-di-ethyl-9-fluorene-2,4,7-tricarbaldehyde.

Seidel P, Schwarzer A, Mazik M Acta Crystallogr E Crystallogr Commun. 2021; 77(Pt 10):1029-1032.

PMID: 34667632 PMC: 8491529. DOI: 10.1107/S2056989021009464.

Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9-Diethylfluorene (Part I).

Seidel P, Mazik M ChemistryOpen. 2020; 9(11):1202-1213.

PMID: 33304735 PMC: 7689417. DOI: 10.1002/open.202000268.

References

Roy Chowdhury S, Mondal S, Muthuraj B, Balaji S, Trivedi V, Iyer P . Remarkably Efficient Blood-Brain Barrier Crossing Polyfluorene-Chitosan Nanoparticle Selectively Tweaks Amyloid Oligomer in Cerebrospinal Fluid and Aβ1-40. ACS Omega. 2018; 3(7):8059-8066. PMC: 6072248. DOI: 10.1021/acsomega.8b00764. View

Saragi T, Spehr T, Siebert A, Fuhrmann-Lieker T, Salbeck J . Spiro compounds for organic optoelectronics. Chem Rev. 2007; 107(4):1011-65. DOI: 10.1021/cr0501341. View

Ie Y, Uchida A, Kawaguchi N, Nitani M, Tada H, Kakiuchi F . Electron-Accepting π-Conjugated Molecules with Fluorine-Containing Dicyanovinylidene as Terminal Groups: Synthesis, Properties, and Semiconducting Characteristics. Org Lett. 2016; 18(17):4320-3. DOI: 10.1021/acs.orglett.6b02070. View

Mazik M . Molecular recognition of carbohydrates by acyclic receptors employing noncovalent interactions. Chem Soc Rev. 2009; 38(4):935-56. DOI: 10.1039/b710910p. View

Oger S, Schapman D, Mougeot R, Leleu S, Lascoux N, Baldeck P . Two-Photon Absorption and Cell Imaging of Fluorene-Functionalized Epicocconone Analogues. Chemistry. 2019; 25(46):10954-10964. DOI: 10.1002/chem.201902731. View

Thomas 3rd S, Joly G, Swager T . Chemical sensors based on amplifying fluorescent conjugated polymers. Chem Rev. 2007; 107(4):1339-86. DOI: 10.1021/cr0501339. View

Marks V, Gottlieb H, Melman A, Byk G, Cohen S, Biali S . Polyethylated aromatic rings: conformation and rotational barriers of 1,2,3,4,5,6,7,8-octaethylanthracene, 1,2,3,4,6,7,8-heptaethylfluorene, and 1,2,3,4,5,6,7,8-octaethylfluorene. J Org Chem. 2001; 66(20):6711-8. DOI: 10.1021/jo0105235. View

Stapf M, Seichter W, Mazik M . Unique hydrogen-bonded complex of hydronium and hydroxide ions. Chemistry. 2015; 21(17):6350-4. DOI: 10.1002/chem.201406383. View

Amrhein F, Lippe J, Mazik M . Carbohydrate receptors combining both a macrocyclic building block and flexible side arms as recognition units: binding properties of compounds with CHOH groups as side arms. Org Biomol Chem. 2016; 14(45):10648-10659. DOI: 10.1039/c6ob01682k. View

10.

Mazik M, Kuschel M . Highly effective acyclic carbohydrate receptors consisting of aminopyridine, imidazole, and indole recognition units. Chemistry. 2008; 14(8):2405-19. DOI: 10.1002/chem.200701269. View

11.

Seidel P, Mazik M . Syntheses of Acyclic and Macrocyclic Compounds Derived from 9,9-Diethylfluorene (Part I). ChemistryOpen. 2020; 9(11):1202-1213. PMC: 7689417. DOI: 10.1002/open.202000268. View

12.

Geffert C, Kuschel M, Mazik M . Molecular recognition of N-acetylneuraminic acid by acyclic pyridinium- and quinolinium-based receptors in aqueous media: recognition through combination of cationic and neutral recognition sites. J Org Chem. 2012; 78(2):292-300. DOI: 10.1021/jo301966z. View

13.

Yang T, Zuo Y, Zhang Y, Gou Z, Wang X, Lin W . Novel fluorene-based fluorescent probe with excellent stability for selective detection of SCN and its applications in paper-based sensing and bioimaging. J Mater Chem B. 2019; 7(30):4649-4654. DOI: 10.1039/c9tb00742c. View

14.

Shaya J, Fontaine-Vive F, Michel B, Burger A . Rational Design of Push-Pull Fluorene Dyes: Synthesis and Structure-Photophysics Relationship. Chemistry. 2016; 22(30):10627-37. DOI: 10.1002/chem.201600581. View

15.

Gabr M, Abdel-Raziq M . Structure-Based Design and Synthesis of Fluorene Derivatives as Novel RORγt Inverse Agonists. Chem Biodivers. 2018; 15(9):e1800244. DOI: 10.1002/cbdv.201800244. View

16.

Spath A, Konig B . Molecular recognition of organic ammonium ions in solution using synthetic receptors. Beilstein J Org Chem. 2010; 6:32. PMC: 2874414. DOI: 10.3762/bjoc.6.32. View

17.

Mazik M, Radunz W, Boese R . Molecular recognition of carbohydrates with acyclic pyridine-based receptors. J Org Chem. 2004; 69(22):7448-62. DOI: 10.1021/jo048979k. View

18.

Mazik M, Konig A . Recognition properties of an acyclic biphenyl-based receptor toward carbohydrates. J Org Chem. 2006; 71(20):7854-7. DOI: 10.1021/jo0610309. View

19.

Mazik M, Geffert C . 8-Hydroxyquinoline as a building block for artificial receptors: binding preferences in the recognition of glycopyranosides. Org Biomol Chem. 2011; 9(7):2319-26. DOI: 10.1039/c0ob00960a. View

20.

Giuseppone N, Fuks G, Lehn J . Tunable fluorene-based dynamers through constitutional dynamic chemistry. Chemistry. 2006; 12(6):1723-35. DOI: 10.1002/chem.200501037. View