214622-81-8

Usage

Uses

Used in Organic Synthesis:
2,7-Pyrenedicarboxylic acid is used as a precursor in the synthesis of various organic compounds, leveraging its reactive carboxylic acid groups for the formation of esters, amides, and other functional groups.
Used in Bioimaging Studies:
As a fluorescent probe, 2,7-PDA is utilized in bioimaging studies to visualize and track specific biological processes or molecules within living organisms, taking advantage of its strong fluorescence under UV light.
Used in Material Science:
2,7-Pyrenedicarboxylic acid is employed in the development of functional organic materials and electronic devices, such as organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs), due to its unique optical and electronic properties.
Used in Environmental Science:
2,7-PDA is of interest to environmental scientists as a marker for identifying sources of PAH pollution, given its presence in atmospheric aerosols. This aids in understanding the environmental impact and potential health risks associated with PAH exposure.

Synthetic route

carbon dioxide (124-38-9) + 2,7-dibromo-4,5,9,10-tetrahydropyrene (102587-98-4) → pyrene-2,7-dicarboxylic acid (214622-81-8)

Conditions	Yield
With n-butyllithium In diethyl ether at -78 - 20℃; Acidic conditions;	96%
Stage #1: 2,7-dibromo-4,5,9,10-tetrahydropyrene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; hexane at 20℃; Inert atmosphere;	91%
With n-butyllithium In tetrahydrofuran at -78℃;

4,4,5,5-tetramethyl-2-[7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyren-2-yl]-1,3,2-dioxaborolane → pyrene-2,7-dicarboxylic acid (214622-81-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(ll) bromide / tetrahydrofuran; methanol; water / 16 h / 90 °C 2: n-butyllithium / diethyl ether / -78 - 20 °C / Acidic conditions View Scheme

pyrene (129-00-0) → pyrene-2,7-dicarboxylic acid (214622-81-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere 2: copper(ll) bromide / tetrahydrofuran; methanol; water / 16 h / 90 °C 3: n-butyllithium / diethyl ether / -78 - 20 °C / Acidic conditions View Scheme
Multi-step reaction with 3 steps 1.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine / tetrahydrofuran / 16 h / 80 °C / Schlenk technique; Inert atmosphere; Sealed tube 2.1: copper(ll) bromide / tetrahydrofuran; methanol; water / 90 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 3.2: 20 °C / Inert atmosphere View Scheme

terbium(III) nitrate pentahydrate + pyrene-2,7-dicarboxylic acid (214622-81-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Tb(2,7-pyrenedicarboxylate)1.5(H2O)2(dimethylformamide)*(dimethylformamide)

Conditions	Yield
In ethanol; water; N,N-dimethyl-formamide suspn. of 2,7-pyrenedicarboxylic acid and Tb nitrate in H2O/EtOH/DMF sonicated (1 min), heated to 80°C in sealed vessel for 24 h, cooled to room temp. at 1°C/min; crystals washed with DMF and EtOH, dried in air; elem. anal.;	73%

zinc nitrate tetrahydrate + pyrene-2,7-dicarboxylic acid (214622-81-8) → Zn4O(pyrene-2,7-dicarboxylate)3

Conditions	Yield
In N,N-dimethyl-formamide soln. ligand and Zn(NO3)2*4H2O in DMF was heated at 70°C for 40 h; hot mother liquor was decanted, rinsed with DMF,product was immersed in CHCl3 for 3 days (solvent was decanted, freshly replenished 3 times), solvent was removed under vac. at room temp.; elem. anal.;

pyrene-2,7-dicarboxylic acid (214622-81-8) + zirconium(IV) chloride (10026-11-6) → 6Zr(4+)*4O(2-)*8HO(1-)*5H2O*6C18H8O4(2-)

Conditions	Yield
With acetic acid In 1-methyl-pyrrolidin-2-one; N,N-dimethyl-formamide at 120℃; for 48h; High pressure;

Upstream product

• 124-38-9 carbon dioxide 
• 102587-98-4 2,7-dibromo-4,5,9,10-tetrahydropyrene 
• 129-00-0 pyrene 

Relevant academic research and scientific papers

Ligand Rigidification for Enhancing the Stability of Metal-Organic Frameworks

Metal-organic frameworks (MOFs) have been developing at an unexpected rate over the last two decades. However, the unsatisfactory chemical stability of most MOFs hinders some of the fundamental studies in this field and the implementation of these materials for practical applications. The stability in a MOF framework is mostly believed to rely upon the robustness of the M-L (M = metal ion, L = ligand) coordination bonds. However, the role of organic linkers as agents of stability to the framework, particularly the linker rigidity/flexibility, has been mostly overlooked. In this work, we demonstrate that a ligand-rigidification strategy can enhance the stability of MOFs. Three series of ligand rotamers with the same connectivity but different flexibility were prepared. Thirteen Zr-based MOFs were constructed with the Zr6O4(OH4)(-CO2)n units (n = 8 or 12) and corresponding ligands. These MOFs allow us to evaluate the influence of ligand rigidity, connectivities, and structure on the stability of the resulting materials. It was found that the rigidity of the ligands in the framework strongly contributes to the stability of corresponding MOFs. Furthermore, water adsorption was performed on some chemically stable MOFs, showing excellent performance. It is expected that more MOFs with excellent stability could be designed and constructed by utilizing this strategy, ultimately promoting the development of MOFs with higher stability for synthetic chemistry and practical applications.

Dysprosium-carboxylate nanomeshes with tunable cavity size and assembly motif through ionic interactions

We report the design of dysprosium directed metallo-supramolecular architectures on a pristine Cu(111) surface. By an appropriate selection of the ditopic molecular linkers equipped with terminal carboxylic groups (TPA, PDA and TDA species), we create reticular and mononuclear metal-organic nanomeshes of tunable internodal distance, which are stabilized by eight-fold Dy?O interactions. A thermal annealing treatment for the reticular Dy:TDA architecture gives rise to an unprecedented quasi-hexagonal nanostructure based on dinuclear Dy clusters, exhibiting a unique six-fold Dy?O bonding motif. All metallo-supramolecular architectures are stable at room temperature. Our results open new avenues for the engineering of supramolecular architectures on surfaces incorporating f-block elements forming thermally robust nanoarchitectures through ionic bonds.

Synthesis of 2-and 2,7-functionalized pyrene derivatives: An application of selective C-H borylation

An efficient synthetic route to 2-and 2,7-substituted pyrenes is described. The regiospecific direct C-H borylation of pyrene with an iridium-based catalyst, prepared in situ by the reaction of [{Ir(μ-OMe)cod}2] (cod=1,5-cyclooctadiene) with 4,4′-di-tert-butyl-2,2′-bipyridine, gives 2,7-bis(Bpin)pyrene (1) and 2-(Bpin)pyrene (2, pin=OCMe 2CMe2O). From 1, by simple derivatization strategies, we synthesized 2,7-bis(R)-pyrenes with R=BF3K (3), Br (4), OH (5), B(OH)2 (6), and OTf (7). Using these nominally nucleophilic and electrophilic derivatives as coupling partners in Suzuki-Miyaura, Sonogashira, and Buchwald-Hartwig cross-coupling reactions, we obtained 2,7-bis(R)-pyrenes with R=(4-CO2C8H17)C6H4 (8), Ph (9), Ca≡CPh (10), Ca≡C[{4-B(Mes)2}C 6H4] (11), Ca≡CTMS (12), Ca≡C[(4-NMe 2)C6H4] (14), Ca≡CH (15), N(Ph)[(4-OMe)C6H4] (16), and R=OTf, R′=Ca≡CTMS (13). Lithiation of 4, followed by reaction with CO2, yielded pyrene-2,7-dicarboxylic acid (17), whilst borylation of 2-tBu-pyrene gave 2-tBu-7-Bpin-pyrene (18) selectively. By similar routes (including Negishi cross-coupling reactions), monosubstituted 2-R-pyrenes with R=BF3K (19), Br (20), OH (21), B(OH)2 (22), [4-B(Mes)2]C 6H4 (23), B(Mes)2 (24), OTf (25), Ca≡CPh (26), Ca≡CTMS (27), (4-CO2Me)C6H4 (28), Ca≡CH (29), C3H6CO2Me (30), OC 3H6CO2Me (31), C3H 6CO2H (32), OC3H6CO2H (33), and O(CH2)12Br (34) were obtained from 2. These derivatives are of synthetic and photophysical interest because they contain donor, acceptor, and conjugated substituents. The crystal structures of compounds 4, 5, 7, 12, 18, 19, 21, 23, 26, and 28-31 have also been obtained from single-crystal X-ray diffraction data, revealing a diversity of packing modes, which are described in the Supporting Information. A detailed discussion of the structures of 1 and 2, their polymorphs, solvates, and co-crystals is reported separately. Copyright