N -Heteroaromatic Fused BODIPY Dimers: Ring-Size Effects from Five- to Six-Membered Rings

Q: What does this research mean for the field?

Six-membered fused BODIPY dimers exhibit panchromatic absorption and enhanced intramolecular charge-transfer behavior compared to five-membered analogues. Novelty: ClaimNovelty.NOVEL_FINDING. Consensus alignment: ConsensusAlignment.NEUTRAL.

Y. D. Zhang; Hao Guan; Qin Duan; Xiong Fu; Limin He; Luyan Tian; Weili Li; Yanni Li; Yanhua Yang; Ye Zou

doi:10.1021/acs.orglett.6c00416

February 26, 2026Organic Letters

N -Heteroaromatic Fused BODIPY Dimers: Ring-Size Effects from Five- to Six-Membered Rings

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Key Points

The research aims to understand how the size of fused N-heterocycles affects the properties of BODIPY dimers. Specifically, it focuses on electronic delocalization and charge transfer characteristics.
Synthesis of three BODIPY dimers with five- and six-membered N-heterocycles.
Utilization of S<sub>N</sub>Ar and C-H activation strategies for synthesis.
Characterization of electronic properties and excited states through spectroscopic techniques.
The six-membered fused BODIPY (PP-di) shows panchromatic absorption and a narrowed HOMO-LUMO gap.
PP-di demonstrates enhanced intramolecular charge-transfer behavior.
Five-membered analogs (Cl-PL-di and PL-di) primarily exhibit localized-excited states.

Implication

Investigates how ring size changes electronic properties in BODIPY dimers, suggesting design improvements for optical materials.

Abstract

Three BODIPY dimers fused with five- and six-membered N-heterocycles were synthesized via an SNAr and C-H activation strategy. N-Heterocycle size enables precise modulation of electronic delocalization and excited-state character. The six-membered fused PP-di exhibits panchromatic absorption, a narrowed HOMO-LUMO gap, and enhanced intramolecular charge-transfer behavior, whereas the five-membered analogues Cl-PL-di and PL-di display predominantly localized-excited states.

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Cite This Study

Zhang et al. (2026) studied this question.

synapsesocial.com/papers/69a3d7baec16d51705d2dfba https://doi.org/10.1021/acs.orglett.6c00416

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N -Heteroaromatic Fused BODIPY Dimers: Ring-Size Effects from Five- to Six-Membered Rings

Key Points

Implication

Abstract

Discussion

Cite This Study

N -Heteroaromatic Fused BODIPY Dimers: Ring-Size Effects from Five- to Six-Membered Rings

Key Points

Implication

Abstract

Discussion

Cite This Study

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