20π-Electron Antiaromatic Benziphthalocyanines with Absorption Reaching the Near-Infrared-II Region.
Chemistry
; 30(29): e202400401, 2024 May 23.
Article
in En
| MEDLINE
| ID: mdl-38488227
ABSTRACT
Although second near-infrared (NIR-II, 1000-1500â
nm) light has attracted considerable attention, especially for life sciences applications, the development of organic dyes with NIR-II absorption remains a formidable challenge. Herein we report the design, synthesis, and electronic properties of 20π-electron antiaromatic benziphthalocyanines (BPcs) that exhibit intense absorption bands in the NIR region. The strong, low-energy absorption of the antiaromatic BPcs is attributed to electric-dipole-allowed HOMO-LUMO transitions with narrow band gaps, enabled by the reduced structural symmetry of BPc compared with regular porphyrins and phthalocyanines. The combination of peripheral substituents and a central metal decreases the HOMO-LUMO energy gaps, leading to the extension of the absorption bands into the NIR-II region (reaching 1100â
nm) under reductive conditions.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Language:
En
Journal:
Chemistry
Journal subject:
QUIMICA
Year:
2024
Document type:
Article
Affiliation country:
Japan
Country of publication:
Germany