Near‐IR Electrochromic Dihydroindolo(2,3a)carbazole‐Based Macrocycles and Their [b]‐Annulated BODIPY Complexes

A new class of redox‐active dihydroindolo(2,3a)carbazole( InC )‐based porphyrin‐like macrocycles (thiophene embedded: InCT and p –phenylene embedded: InCB ) and the corresponding [b]‐annulated BODIPY complexes ( InCT BF 2  and InCB BF 2 ) are reported. A facile synthetic methodology is adopted to ac...

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Bibliographic Details
Published in:Advanced optical materials 2023-11, Vol.11 (21)
Main Authors: Spergen, Aswini, Kalaiselvan, Arumugam, Gokulnath, Sabapathi
Format: Article
Language:English
Subjects:
Carbazoles
Electrochromism
Materials science
NMR
Nuclear magnetic resonance
Optics
Porphyrins
Room temperature
Rotation
Single crystals
Stability
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Summary:A new class of redox‐active dihydroindolo(2,3a)carbazole( InC )‐based porphyrin‐like macrocycles (thiophene embedded: InCT and p –phenylene embedded: InCB ) and the corresponding [b]‐annulated BODIPY complexes ( InCT BF 2  and InCB BF 2 ) are reported. A facile synthetic methodology is adopted to accomplish the new expanded‐porphyrin‐like macrocyclic systems using the key precursor 11  based on 11,12‐dihydroindolo(2,3a)carbazole building block 4 . In these macrocyclic systems, the subunit 4  is deemed to be a donor and an azafulvene‐extended with π ‐conjugated fragment (thiophene or p ‐phenylene) acts as an acceptor. Single crystal X‐ray structures are obtained for both InCT and InCB . Spectroelectrochemical studies on these macrocycles and their BF 2  complexes display intriguing near‐IR electrochromic properties with reversible multi‐color switching upon cathodic scans at room temperature. InCT BF 2  shows high stability with a radical comproportionation constant ( K c ) of 1.22 × 10 6 . Thiophene and p ‐phenylene subunits in InCT and InCB exhibit ring rotation at room temperature as evident from NMR studies. Such ring rotation is restricted upon BF 2  complexation, and they show unusual stability in acidic conditions.
ISSN:2195-1071
2195-1071
DOI:10.1002/adom.202300778