Remarkable red-shift in absorption and emission of linear BODIPY oligomers containing thiophene linkers

Saino, Sousuke; Saikawa, Makoto; Nakamura, Takashi; Yamamura, Masato; Nabeshima, Tatsuya

doi:10.1016/j.tetlet.2016.03.003

Cited by 16 publications

(29 citation statements)

References 34 publications

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“…This effect is enhanced when the 2‐thien‐2‐yl‐substituted BODIPYs 13 and 16 are regarded, showing red shifts of approximately 140 nm and 160 nm, respectively, for the absorptions and emissions (related to 20 ). This is in line with similar studies in which a 2‐thien‐2‐yl substitution is reported to induce a red shift of about 60–70 nm, that is further enhanced in our compounds due to the 3‐methoxy groups. A red shift by substitution at C‐3 has likewise been observed for bromo‐substituted BODIPYs, however, the influence of the electron‐donating methoxy groups seems to be more pronounced .…”

Section: Resultsmentioning

confidence: 99%

Novel Alkoxy‐Substituted Dipyrrins and Near‐IR BODIPY Dyes—Preparation and Photophysical Properties

Schoder

Kalai

Reißig

2017

Chemistry A European J

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Starting from 3-alkoxy-2-aryl-substituted pyrroles and aromatic aldehydes, a collection of new dipyrrins was prepared. Under the standard conditions of Treibs, these were converted into the corresponding boron dipyrrins (BODIPYs). Compounds of this type with alkoxy groups at C-3 position of both pyrrole subunits are new and hence the photophysical properties of this collection of novel dipyrrins and BODIPY dyes were investigated. The dipyrrins show absorption maxima up to 596 nm and emissions of up to 677 nm. For the BODIPY series a remarkable effect of the alkoxy groups was identified, resulting in red shifts for absorptions and emissions. The compound substituted with two 2-thien-2-yl groups and a meso-C F substituent shows an absorption maximum at 725 nm and emits at 754 nm and thus is a new representative of a near-IR BODIPY dye related to certain aza-BODIPYs. Our results demonstrate the influence of the alkoxy groups on the spectroscopic data and reveal the potential of 3-alkoxy-2-aryl-substituted pyrroles for the design of new fluorophores.

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Section: Resultsmentioning

confidence: 99%

Novel Alkoxy‐Substituted Dipyrrins and Near‐IR BODIPY Dyes—Preparation and Photophysical Properties

Schoder

Kalai

Reißig

2017

Chemistry A European J

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“…36,[46][47][48][49][50][51][52] Nabeshima and coworkers have synthesized a series of thiophenyl BODIPY derivatives L6BF 2 -L15(BF 2 ) 3 to investigate the relationship between the structure and emission properties ( Figure 2). 53 As a result, several findings were obtained (see Figure 3 for the numbering of the atoms of the BODIPY nucleus). (1) Introduction of the thiophenyl groups at the 3,5-positions of the BODIPY achieved a strong fluorescence in the red region (e.g.,  em = 643 nm (Φ F = 0.78) for L7BF 2 ).…”

Section: Linear Oligomers Of Boron-dipyrrin Complexesmentioning

confidence: 97%

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Chiba¹,

Nakamura²,

Matsuoka³

et al. 2020

Synlett

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The dipyrrin–metal complexes and especially the boron complex 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) have recently attracted considerable attention because of their interesting properties and possible applications. We have developed two unique and useful ways to extend versatility and usefulness of the dipyrrin complexes. The first one is the linear and macrocyclic oligomerization of the BODIPY units. These arrangements of the B–F moieties of the oligomerized BODIPY units provide sophisticated functions, such as unique recognition ability toward cationic guest, associated with changes in the photophysical properties by utilizing unprecedented interactions between the B–F and a cationic species. The second one is introduction of additional ligating moieties into the dipyrrin skeleton. The multidentate N2Ox dipyrrin ligands thus obtained form a variety of complexes with 13 and 14 group elements, which are difficult to synthesize using the original N2 dipyrrin derivatives. Interestingly, these unique complexes exhibit novel structures, properties, and functions such as guest recognition, stimuli-responsive structural conversion, switching of the optical properties, excellent stability of the neutral radicals, etc. We believe that these multifunctional dipyrrin complexes will advance the basic chemistry of the dipyrrin complexes and develop their applications in the materials and medicinal chemistry fields.1 Introduction2 Linear Oligomers of Boron–Dipyrrin Complexes3 Cyclic Oligomers of Boron–Dipyrrin Complexes4 A Cyclic Oligomer of Zinc–Dipyrrin Complexes5 Group 13 Element Complexes of N2Ox Dipyrrins6 Chiral N2 and N2Ox Dipyrrin Complexes7 Group 14 Element Complexes of N2O2 Dipyrrins8 Other N2O2 Dipyrrin Complexes with Unique Properties and Functions9 Conclusion

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“…Selectedphotophysicaldata for the final compounds. [a] The photophysical properties of meso-phenyl-1,3,5,7-tetramethylB ODIPY Ph-TMBDP (entry1), [42] tetraphenyl-aza-BODIPY aza-BDP (entry 5), [40] and meso-phenyl-3,5-dithienyl BODIPY Ph-THBDP (entry 9) [41] were added for comparison.…”

Section: Photophysical Propertiesmentioning

confidence: 99%

“…[%] [43] [c] Data for Ph-THBDP are reported in the literature in CHCl 3 (see ref. [41]). Chem.E ur.J.…”

Section: Entrymentioning

confidence: 99%

“…Compounds 9-11 have Stokes shifts of 40-42 nm (entries 6-8), around 10 nm larger than aza-BDP (32 nm), whereas compound 13 shows the same Stokes shiftasPh-THBDP It is worth noting that our systemss how very different fluorescentq uantum yields (F F )d epending on the type of BODIPY core;B ODIPY derivatives 2-4 exhibit the highest values with F F around4 0-42 %, though weakert han Ph-TMBDP (56%), whereas aza-BODIPYd erivatives 9-11 show low F F (1.4-1.5 %), which is also slightly lower,b ut similart ot he aza-BDP (1.9 %). It is known from the literature that not all the 3,5-dithienyl BODIPYsa re strongly fluorescent; [41] most of them functionalized at their meso-positions were reported to have low fluorescence efficiencies. Nevertheless,t he meso-phenyl-3,5-dithienyl BODIPY (Ph-THBDP)r epresents an exception with aq uantum yield of 84 %.…”

Section: Entrymentioning

confidence: 99%

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Carborane‐BODIPY Dyads: New Photoluminescent Materials through an Efficient Heck Coupling

Bellomo

Chaari

Cabrera‐González

et al. 2018

Chemistry A European J

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A small library of carborane-BODIPY/aza-BODIPY dyads were efficiently synthesized by means of a novel convergent synthetic approach, the key step of which is a Pd-catalyzed Heck coupling reaction. The structural characterization and photoluminescence properties of the newly synthesized dyads were evaluated. The presence of the carborane did not significantly alter the photophysical patterns of the BODIPY or aza-BODIPY in the final fluorophores, but it produced a decrease of the emission fluorescent quantum yields that was in the range from 1.4 % for aza-BODIPY to 48 % for BODIPY-dyads. The carborane-BODIPY dyads were successfully incorporated into cells, especially compounds 2, 4 and 13, demonstrating their cytoplasmic localization. The fluorescent and biocompatibility properties make these compounds good candidates for in vitro cell tracking.

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Remarkable red-shift in absorption and emission of linear BODIPY oligomers containing thiophene linkers

Cited by 16 publications

References 34 publications

Novel Alkoxy‐Substituted Dipyrrins and Near‐IR BODIPY Dyes—Preparation and Photophysical Properties

Novel Alkoxy‐Substituted Dipyrrins and Near‐IR BODIPY Dyes—Preparation and Photophysical Properties

Synthesis and Functions of Oligomeric and Multidentate Dipyrrin Derivatives and their Complexes

Carborane‐BODIPY Dyads: New Photoluminescent Materials through an Efficient Heck Coupling

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