<b>2-Bora- and 2-Thia-1,3-diazaazulenes</b>

Holmquist, H. E.; Benson, R. E.

doi:10.1021/ja00883a021

Cited by 10 publications

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“…Although fluorescence was noted for BF2 complexes H [23] and J [24] from l-amin0-7-imino-l,3,5-~y-cloheptatrienes and 8-amino-and 8-hydroxyquinoline these complexes were not examined for laser activity. BF2 complexes with less unsaturation, for example, the hexahydropyrromethene-BF2 complex K with A,,, (C2H50H) 320 nm (log E 4.4) [25], were not examined for fluorescence (<400 nm) and laser activity.…”

Section: Background Informationmentioning

confidence: 99%

Pyrromethene–BF₂ complexes as laser dyes:1.

Shah

Thangaraj

Soong

et al. 1990

Heteroatom Chemistry

244

172

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Condensations between 3‐X‐2,4‐dimethylpyrroles (X = H, CH3, C2H5, and CO2C2H5) and acyl chlorides gave derivatives of 3,5,3′,5′‐tetramethylpyrromethene (isolated as their hydrochloride salts): 6‐methyl, 6‐ethyl, 4,4′,6‐trimethyl, 4,4′‐diethyl‐6‐methyl, and 4,4′‐dicarboethoxy‐6‐ethyl derivatives for conversion on treatment with boron trifluoride to 1,3,5,7‐tetramethylpyrromethene–BF2 complex (TMP–BF2) and its 8‐methyl (PMP–BF2), 8‐ethyl, 2,6,8‐trimethyl (HMP–BF2),2,6,‐diethyl‐8‐methyl (PMDEP–BF2), and 2,6‐dicarboethoxy‐8‐ethyl derivatives. Chlorosulfonation converted, 1,3,5,7,8‐pentamethylpyrromethene–BF2 complex to its 2,6‐disulfonic acid isolated as the lithium, sodium (PMPDS–BF2), potassium, rubidium, cesium, ammonium, and tetramethylammonium disulfonate salts and the methyl disulfonate ester. Sodium 1,3,5,7‐tetramethyl‐8‐ethylpyrromethene‐2,6‐disulfonate–BF2 complex was obtained from the 8‐ethyl derivative of TMP–BF2. Nitration and bromination converted PMP–BF2 to its 2,6‐dinitro‐(PMDNP–BF2) and 2,6‐dibromo‐ derivatives. The time required for loss of fluorescence by irradiation from a sunlamp showed the following order for P–BF2 compounds (10−3 to 10−4 M) in ethanol: PMPDS–BF2, 7 weeks; PMP–BF2, 5 days; PMDNP–BF2, 72 h; HMP–BF2, 70 h; and PMDEP–BF2, 65 h. Under similar irradiation PMPDS–BF2 in water lost fluorescence after 55 h. The dibromo derivative was inactive, but each of the other pyrromethene–BF2 complexes under flashlamp excitation showed broadband laser activity in the region λ 530–580 nm. In methanol PMPDS–BF2 was six times more resistant to degradation by flashlamp pulses than was observed for Rhodamine‐6G (R‐6G). An improvement (up to 66%) in the laser power efficiency of PMPDS–BF2 (10−4 M in methanol) in the presence of caffeine (a filter for light <300 nm) was dependent on flashlamp pulse width (2.0 to 7.0 μsec).

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Section: Background Informationmentioning

confidence: 99%

Pyrromethene–BF₂ complexes as laser dyes:1.

Shah

Thangaraj

Soong

et al. 1990

Heteroatom Chemistry

244

172

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“…23 As reported in the literature, 2-aminotroponimine derivatives are known to form a stable complex with BF 2 . 24 However, dipyrromethene is a versatile N,N-ligand of boron, and has been used for the synthesis of various fluorescent BODIPY molecules. [25][26][27] The non-dipyrromethene scaffold has also been used for the synthesis of BODIPY type fluorescent molecules, and BODIPY analogues, by N,N-/N,Ochelation.…”

Section: Introductionmentioning

confidence: 99%

A new amino acid, hybrid peptides and BODIPY analogs: synthesis and evaluation of 2-aminotroponyl-l-alanine (ATA) derivatives

Gupta

Sharma

2022

Org. Biomol. Chem.

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Borchelate und Bormetallchelate, II. Über die Bildung von Fluorborchelaten

1973

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Durch Vergleich der Reaktionsweisen ahnlicher und gezielt abgeanderter Chelatbildner bei Umsetzungen mit BF3 wird gezeigt, daR die gegenuber den Diphenylborchelaten erschwerte Bildung von Difluorhorchelaten nur dann eintritt, wenn Mesomericstabilisierung irn Chelatring mijglich ist und/odcr andere Faktoren die Bildung begunstigen. Aus den UV-Spektren kann man auf die relative Stabilitat der Chelatringe schlienen. Difluorborchelate wurden von folgenden Chelatbildnern dargestellt: 2-Hydroxyacetophenon (1)2,3), Salicylaldehyd (2), N-Benzoyl-N-phenylhydroxylamin (17). 2,2'-Pyridoin hildet mit BF3 das Bis(difluorbor)-Chelat 14, wahrend N-Salicylidenanthranilsaure und 2-(Sahcylidenamino)phenol die Monofluorbor-Chelate 10 und 11 ergeben. In den Monofluorbor-Chelaten ist das Boratom an zwei Chelatringen beteiligt. BF3-Addukte wurden von N-Salicylidenanilin (6), 2-Aminophenol (12) und 2-(Benzylidenamino)phenol (13) isoliert. 5-Hydroxy-7-methoxyflavon (3), N-Salicylidenanilin (4), N-[l-(2-Hydroxyphenyl)iithyliden]anilin (5), Salicylaldehydazin (7), Salicylaldehyd-phenylhydrazon (S), 2-Hydroxyacetophenonphenylhydrazon (9), I-Benzolazo-2-naphthol (15)4), 1-Benzolazo-2-naphthylamin (16) und

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2-Bora- and 2-Thia-1,3-diazaazulenes

Cited by 10 publications

References 0 publications

Pyrromethene–BF₂ complexes as laser dyes:1.

Pyrromethene–BF₂ complexes as laser dyes:1.

A new amino acid, hybrid peptides and BODIPY analogs: synthesis and evaluation of 2-aminotroponyl-l-alanine (ATA) derivatives

Borchelate und Bormetallchelate, II. Über die Bildung von Fluorborchelaten

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2-Bora- and 2-Thia-1,3-diazaazulenes

Cited by 10 publications

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Pyrromethene–BF2 complexes as laser dyes:1.

Pyrromethene–BF2 complexes as laser dyes:1.

A new amino acid, hybrid peptides and BODIPY analogs: synthesis and evaluation of 2-aminotroponyl-l-alanine (ATA) derivatives

Borchelate und Bormetallchelate, II. Über die Bildung von Fluorborchelaten

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Pyrromethene–BF₂ complexes as laser dyes:1.

Pyrromethene–BF₂ complexes as laser dyes:1.