Highly soluble cyclic dibenzophenazine heterodimer enabled by a tetra-functionalized building block

Naohiro Namba; Fumiya Ogura; Marc K Etherington; Satoshi Minakata; Youhei Takeda

doi:10.1093/chemle/upaf216

Highly soluble cyclic dibenzophenazine heterodimer enabled by a tetra-functionalized building block

Naohiro Namba, Fumiya Ogura, Marc K Etherington, Satoshi Minakata^*, Youhei Takeda^*

^*Corresponding author for this work

School of Engineering Physics and Mathematics

Research output: Contribution to journal › Article › peer-review

Abstract

A cyclic heterodimer of dibenzo[a, j]phenazine (DBPHZ) has been synthesized using a novel tetra-functionalized DBPHZ building block bearing bulky siloxy and dibromo substituents. Siloxy groups markedly enhanced the solubility of both the resulting intermediates and the macrocycle, enabling facile purification and systematic photophysical studies. The heterodimer exhibits locally excited fluorescence with minimal solvent dependence in solutions and pronounced aggregation-induced red-shifted emission in the films. This study demonstrates a molecular design strategy to enhance solubility and processability of nitrogen-embedded π-conjugated macrocycles.

Original language	English
Article number	upaf216
Pages (from-to)	1-5
Number of pages	5
Journal	Chemistry Letters
Volume	54
Issue number	12
Early online date	25 Nov 2025
DOIs	https://doi.org/10.1093/chemle/upaf216
Publication status	Published - 31 Dec 2025

Keywords

heteroaromatic compound
π-conjugated macrocycle
solubility

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title = "Highly soluble cyclic dibenzophenazine heterodimer enabled by a tetra-functionalized building block",

abstract = "A cyclic heterodimer of dibenzo[a, j]phenazine (DBPHZ) has been synthesized using a novel tetra-functionalized DBPHZ building block bearing bulky siloxy and dibromo substituents. Siloxy groups markedly enhanced the solubility of both the resulting intermediates and the macrocycle, enabling facile purification and systematic photophysical studies. The heterodimer exhibits locally excited fluorescence with minimal solvent dependence in solutions and pronounced aggregation-induced red-shifted emission in the films. This study demonstrates a molecular design strategy to enhance solubility and processability of nitrogen-embedded π-conjugated macrocycles.",

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author = "Naohiro Namba and Fumiya Ogura and Etherington, \{Marc K\} and Satoshi Minakata and Youhei Takeda",

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day = "31",

doi = "10.1093/chemle/upaf216",

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T1 - Highly soluble cyclic dibenzophenazine heterodimer enabled by a tetra-functionalized building block

AU - Namba, Naohiro

AU - Ogura, Fumiya

AU - Etherington, Marc K

AU - Minakata, Satoshi

AU - Takeda, Youhei

PY - 2025/12/31

Y1 - 2025/12/31

N2 - A cyclic heterodimer of dibenzo[a, j]phenazine (DBPHZ) has been synthesized using a novel tetra-functionalized DBPHZ building block bearing bulky siloxy and dibromo substituents. Siloxy groups markedly enhanced the solubility of both the resulting intermediates and the macrocycle, enabling facile purification and systematic photophysical studies. The heterodimer exhibits locally excited fluorescence with minimal solvent dependence in solutions and pronounced aggregation-induced red-shifted emission in the films. This study demonstrates a molecular design strategy to enhance solubility and processability of nitrogen-embedded π-conjugated macrocycles.

AB - A cyclic heterodimer of dibenzo[a, j]phenazine (DBPHZ) has been synthesized using a novel tetra-functionalized DBPHZ building block bearing bulky siloxy and dibromo substituents. Siloxy groups markedly enhanced the solubility of both the resulting intermediates and the macrocycle, enabling facile purification and systematic photophysical studies. The heterodimer exhibits locally excited fluorescence with minimal solvent dependence in solutions and pronounced aggregation-induced red-shifted emission in the films. This study demonstrates a molecular design strategy to enhance solubility and processability of nitrogen-embedded π-conjugated macrocycles.

KW - heteroaromatic compound

KW - π-conjugated macrocycle

KW - solubility

UR - https://www.scopus.com/pages/publications/105023882602

U2 - 10.1093/chemle/upaf216

DO - 10.1093/chemle/upaf216

M3 - Article

SN - 0366-7022

VL - 54

SP - 1

EP - 5

JO - Chemistry Letters

JF - Chemistry Letters

IS - 12

M1 - upaf216

ER -

Highly soluble cyclic dibenzophenazine heterodimer enabled by a tetra-functionalized building block

Abstract

Keywords

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