Extended Benzene‐Fused Oligo‐BODIPYs: In Three Steps to a Series of Large, Arc‐Shaped, Near Infrared Dyes
TLDR
FeCl3 serves as an efficient, bifunctional oxidant for a (multiple) cyclization/desaturation process, applied to ethylene‐bridged dimeric, trimeric and oligomeric species to transform linking ethano units into stiff benzene fusions between unsubstituted β‐positions of each BODIPY unit.Abstract:
We present a straightforward, three-step synthesis engaging an oligomerization and subsequent one-pot oxidation step to form fully conjugated, benzene-fused oligo-BODIPYs from simple BODIPY precursors. FeCl3 serves as an efficient, bifunctional oxidant for a (multiple) cyclization/desaturation process, applied to ethylene-bridged dimeric, trimeric and oligomeric species to transform linking ethano units into stiff benzene fusions between unsubstituted β-positions of each BODIPY unit. The structural integrity was verified by X-ray crystallography, and all target compounds were studied in detail by photophysical, electrochemical and computational means. The main S1 excited state gradually converges to a structure-specific excitation limit, displaying a strong shift of the absorption event from about 500 nm (BODIPY monomer) to 955 nm (octamer) with attenuation coefficients up to ca. 500 000 M-1 cm-1 .read more
Citations
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Near-infrared dyes for two-photon absorption in the short-wavelength infrared: strategies towards optical power limiting
TL;DR: The common strategies and main structure-property relationships that lead to near-infrared (NIR) electronic absorption of chromophores are described and a complete review of the molecules that feature two-photon absorption (2PA) beyond 1100 nm is presented.
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Double π-Extended Undecabenzo[7]helicene.
TL;DR: The double π-extended undecabenzohelicene (DHE) as discussed by the authors is a chiral nanographene composed of 65 fused rings and 186 conjugated carbon atoms.
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Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers.
Zhaoyang Zhu,Xue Zhang,Xing Guo,Qinghua Wu,Zhongxin Li,Changjiang Yu,Erhong Hao,Lijuan Jiao,Jianzhang Zhao +8 more
TL;DR: In this article, a cyclic trimeric BODIPY array with a lifetime up to 257.5 μs was generated from easily accessible meso-mesityldipyrrinone and arylboronic acids in one pot.
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Rhodium-catalyzed annulation of pyrrole substituted BODIPYs with alkynes to access π-extended polycyclic heteroaromatic molecules and NIR absorption
Bixiang Zhou,Mengjie Guo,Qingjie Pan,Mingbo Zhou,Ling Xu,Yutao Rao,Kaisheng Wang,Bangshao Yin,Jie Zhou,Jianxin Song +9 more
TL;DR: A series of π-extended BODIPY derivatives fused with an indolizine scaffold were prepared smoothly via rhodium-catalyzed C-H functionalization/annulation with excellent chemoselectivity and regioselectivities, where the pyrrole moiety serves as a directing group as mentioned in this paper.
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Near-infrared upper phenyl-fused BODIPY as a photosensitizer for photothermal-photodynamic therapy.
T. Yu,Dongxiang Zhang,Jie Wang,Chang‐Liang Sun,Tianfang Cui,Zhangrun Xu,Xin Jiang,Jianjun Du +7 more
TL;DR: In this article, an upper ring-fused BODIPY with 4-dimethylaminostyryl groups (BBDP) was designed and synthesized for photothermal-photodynamic therapy.
References
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Journal ArticleDOI
BODIPY dyes and their derivatives: syntheses and spectroscopic properties.
Aurore Loudet,Kevin Burgess +1 more
Journal ArticleDOI
The Chemistry of Fluorescent Bodipy Dyes: Versatility Unsurpassed
TL;DR: The Bodipy family, first developed as luminescent tags and laser dyes, has become a cornerstone for these new applications and the near future looks extremely bright for "porphyrin's little sister".
Journal ArticleDOI
Fluorescent indicators based on BODIPY
TL;DR: This critical review covers the advances made using the 4-bora-3a,4a-diaza-s-indacene (BODIPY) scaffold as a fluorophore in the design, synthesis and application of fluorescent indicators for pH, metal ions, anions, biomolecules, reactive oxygen species, reactive nitrogen species, redox potential, chemical reactions and various physical phenomena.
Journal ArticleDOI
BODIPY dyes in photodynamic therapy.
TL;DR: The attributes of BODIPY dyes for PDT are summarized, and substituents with appropriate oxidation potentials are summarized in some related areas.
Journal ArticleDOI
New advances in nanographene chemistry
TL;DR: Recent progress in the "bottom-up" chemical syntheses of structurally well-defined nanographenes, namely graphene molecules and GNRs are described.
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