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Principles Of Fluorescence Spectroscopy

J-aggregation is an efficient strategy for the development of fluorescent imaging agents in the second near-infrared window. However, the design of the second near-infrared fluorescent J-aggregates is challenging due to the lack of suitable J-aggregation dyes. Herein, we report meso-[2.2]paracyclophanyl-3,5-bis-N,N-dimethylaminostyrl BODIPY (PCP-BDP2) as an example of BODIPY dye with J-aggregation induced the second near-infrared fluorescence. PCP-BDP2 shows an emission maximum at 1010 nm in the J-aggregation state. Mechanism studies reveal that the steric and conjugation effect of the PCP group on the BODIPY play key roles in the J-aggregation behavior and photophysical properties tuning. Notably, PCP-BDP2 J-aggregates can be utilized for lymph node imaging and fluorescence-guided surgery in the nude mouse, which demonstrates their potential clinical application. This study demonstrates BODIPY dye as an alternate J-aggregation platform for developing the second near-infrared imaging agents. J-aggregation has been proved to be an efficient strategy for the development of fluorescent imaging agents in the NIR-II spectral region but the design of appropriate J-aggregates is challenging. Here, the authors demonstrate J-aggregation of a BODIPY dye with NIR-II emission and demonstrate lymph node imaging for fluorescence guided surgery.

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J-aggregates of meso-[2.2]paracyclophanyl-BODIPY dye for NIR-II imaging.

Far-red and near-infrared (NIR) absorbing/emitting dyes have found diverse applications in biomedicine and material science. However, the absorption and emission of classical BODIPY chromophores at short wavelength hamper their applications. Several strategies have been adopted to modify the structure of the BODIPY core to design NIR dyes. Among these, the most efficient approach to expand the π-conjugation of the BODIPY core is via fusion of aromatic rings. So far, many novel BODIPY skeletons fused to aromatic hydrocarbons and heterocycles at the b bond have been reported. This review comprehensively describes the recent advances regarding the development of aromatic [b]-fused BODIPY dyes with the focus on the design and synthesis, the relationships between their photophysical/spectroscopic properties and molecular structures, and the potential applications in bioassays and optoelectronic devices.

Aromatic [b]-fused BODIPY dyes as promising near-infrared dyes.

This work provides an overview of the recent advances in the field of two-photon absorbing chromophores active in the short-wavelength infrared (SWIR) spectral range. Herein the common strategies and main structure–property relationships that lead to near-infrared (NIR) electronic absorption of chromophores are described. A complete review of the molecules that feature two-photon absorption (2PA) beyond 1100 nm is presented for the purpose of further use in optical power limiting applications in the SWIR band. Recent progress in the development of optical power limiting in this particular spectral region is reported with emphasis on the use of the two-photon induced excited state absorption (ESA) process as an optical power limiting enhancer.

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Near-infrared dyes for two-photon absorption in the short-wavelength infrared: strategies towards optical power limiting

Optical imaging, especially fluorescence and photoacoustic imaging, is a non-invasive imaging approach with high spatial and temporal resolution and high sensitivity, compared to positron emission tomography (PET) or magnetic resonance imaging (MRI). Due to the merits of imaging using the second near-infrared (NIR-II) window, like deeper penetration depth, high signal-to-noise ratio, high resolution, and low tissue damage, researchers have devoted great effort to developing contrast agents with NIR-II absorption or emission. In this Review, we summarize recently developed organic luminescent and photoacoustic materials, ranging from small molecules to conjugated polymers. Then, we systematically introduce engineering strategies and describe the imaging performance classified by the skeleton cores. Finally, we elucidate the challenges and prospects of these NIR-II organic dyes for potential clinical applications. We expect our summary can inspire researchers to expand the spectrum of NIR-II contrast agents for diverse bioapplications. 

The Chemistry of Organic Contrast Agents in the NIR‐II Window

Visible-Light Excitation of BODIPYs Enables Self-Promoted Radical Arylation at Their 3,5-Positions with Diazonium Salts

Strategic Construction of Ethene-Bridged BODIPY Arrays with Absorption Bands Reaching the Near-Infrared II Region.

A convenient procedure for the preparation of functionalized BODIPYs bearing both F and an organo substituent at the boron center, using one-pot reactions between in situ formed dipyrromethenes and organotrifluoroborate salts, has been reported. The complexation reaction utilizes stable and commercial accessible organotrifluoroborate potassium salts and provides a facile access to a variety of novel B-functionalized BODIPYs, which are hard to access through current synthetic methods.

Organotrifluoroborate Salts as Complexation Reagents for Synthesizing BODIPY Dyes Containing Both Fluoride and an Organo Substituent at the Boron Center.

A new class of hybridized and core-contracted porphyrinoids, B(III)-submonoazaporphyrins, which may be viewed as the hybrids of B(III)-subporphyrins and B(III)-subporphyrazines, was reported. The versatile single-step synthesis was based on an efficient intramolecular nucleophilic substitution reaction on readily available α-amino-α'-bromotripyrromethenes, while boronic acids, trifluoroborate salts, or trimethoxyborate simultaneously acted as the template and provider of apical substituent. Those new hybrids, as robust and photostable compounds, were fully characterized by NMR, mass spectrometry, and X-ray crystallography. They showed intense absorption and emission in the visible region, and their electrochemical properties and computational calculation are also discussed.

Zhengxin Kang

Papers

Visible-Light Excitation of BODIPYs Enables Self-Promoted Radical Arylation at Their 3,5-Positions with Diazonium Salts

Strategic Construction of Ethene-Bridged BODIPY Arrays with Absorption Bands Reaching the Near-Infrared II Region.

Organotrifluoroborate Salts as Complexation Reagents for Synthesizing BODIPY Dyes Containing Both Fluoride and an Organo Substituent at the Boron Center.

Boron-Templated Synthesis of B(III)-Submonoazaporphyrins: The Hybrids of B(III)-Subporphyrins and B(III)-Subporphyrazines.

Palladium(II)-Catalyzed Dehydrogenative Strategy for Direct and Regioselective Oligomerization of BODIPY Dyes.