A Cyclic <i>tris</i> -BODIPY Complex Derived from Dithienopyrrole Embedded [48]Dodecaphyrin (1.0.0.1.0.0.1.0.0) as Photoacoustic Contrast Agent

A rigid dithienopyrrole embedded dodecaphyrin and its <i>tris</i>-BODIPY (bis(triisopropylsilyl-ethynyl)-substituted boron-dipyrromethene (BODIPY)) complex have been synthesized. DFT analysis showed a "<i>ruffled</i>" structure for dodecaphyrin and a <i>saddle</i>-shaped structure for <i>tris</i>-BODIPY. Increased conjugation of <i>tris</i>-BODIPY <b>2</b> showed a red-shifted absorption band (ca. 115 nm) with strong absorption in the NIR-I region as compared to its freebase analogue <b>1</b>. These optical features along with nonfluorescent characteristics of <b>2</b> displayed an efficient photoacoustic imaging contrast agent.

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Publication Details

Journal
Organic Letters
Published
2025-12-09
DOI
https://doi.org/10.1021/acs.orglett.5c04304
Primary Topic
Luminescence and Fluorescent Materials
Type
article
Field-Weighted Citation Impact
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article

A Cyclic tris -BODIPY Complex Derived from Dithienopyrrole Embedded [48]Dodecaphyrin (1.0.0.1.0.0.1.0.0) as Photoacoustic Contrast Agent

Thondikkal Sulfikarali, Deepayan Samanta, Sabapathi Gokulnath, Aathira Edwin et al.
Organic Letters
Luminescence and Fluorescent Materials
article

A Cyclic tris -BODIPY Complex Derived from Dithienopyrrole Embedded [48]Dodecaphyrin (1.0.0.1.0.0.1.0.0) as Photoacoustic Contrast Agent

Thondikkal Sulfikarali, Deepayan Samanta, Sabapathi Gokulnath, Aathira Edwin, Jayaprakash Ajay, Mayanglambam Suheshkumar Singh, Gayathri Krishnan
article en

Abstract

A rigid dithienopyrrole embedded dodecaphyrin and its <i>tris</i>-BODIPY (bis(triisopropylsilyl-ethynyl)-substituted boron-dipyrromethene (BODIPY)) complex have been synthesized. DFT analysis showed a "<i>ruffled</i>" structure for dodecaphyrin and a <i>saddle</i>-shaped structure for <i>tris</i>-BODIPY. Increased conjugation of <i>tris</i>-BODIPY <b>2</b> showed a red-shifted absorption band (ca. 115 nm) with strong absorption in the NIR-I region as compared to its freebase analogue <b>1</b>. These optical features along with nonfluorescent characteristics of <b>2</b> displayed an efficient photoacoustic imaging contrast agent.

Organic LettersVol. 27(50)
Indian Institute of Science Education and Research Thiruvananthapuram (IN)
Openalex Percentile: Top 68%
Luminescence and Fluorescent Materials
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A Cyclic <i>tris</i> -BODIPY Complex Derived from Dithienopyrrole Embedded [48]Dodecaphyrin (1.0.0.1.0.0.1.0.0) as Photoacoustic Contrast Agent — Thondikkal Sulfikarali, Deepayan Samanta, et al. · Organic Letters (2025) | TGRS Research Map | TGRS