ChemInform Abstract: SYNTHESIS AND STUDY OF TRICARBOCYANINES CONTAINING FIVE‐ AND SIX‐MEMBERED RINGS IN CHROMOPHORE

Abstract

Die durch Einführung fünf‐ oder sechsgliedriger Ringe in die Polymethinkette bewirkte bathochrome Verschiebung der Absorptionsmaxima beträgt für die Thiatricarbocyanine (IVa) und (VII) etwa 45 bzw. 5 nm, für die Chinotricarbocyanine (Va) etwa 68 bzw. 20 nm.

Functionalized Tricarbocyanine Dyes as Near-Infrared Fluorescent Probes for Biomolecules

“…General Synthesis. The functionalized tricarbocyanine dyes were synthesized using modifications of previously described procedures (11,(14)(15)(16)(17)(18)(19)(20)(21).…”

Functionalization of benzo[c,d]indole system for the synthesis of visible and near‐infrared dyes

“…In this two‐step preparation the substrate 4 was treated with the Vilsmeier‐Haack reagent 9 [8] in acetic anhydride in the presence of sodium acetate as a base catalyst to furnish a chloro‐substituted cyanine 10 , which then was transformed to 8=O by the reaction with N ‐hydroxysuccinimide. The mechanism of this highly efficient transformation has been discussed previously [7].…”

“…The Vilsmeier‐Haack reagent 9 was obtained as reported previously [8]. Condensation of 9 with 4 was conducted in ethanol in the presence of sodium acetate by using a general procedure [10].…”

“…A solution of inner salt 13 (303 mg, 1 mmol) Vilsmeier‐Haack reagent 9 [8] (180 mg, 0.5 mmol), and sodium acetate (82 mg, 1 mmol) in acetic anhydride (20 mL) was heated under reflux for 8 h, then cooled and treated with ether (30 mL). The resultant precipitate of cyanine 14 was crystallized from methanol/ether; yield 115 mg (30%); mp > 300°C; 1 H NMR (deuterated dimethyl sulfoxide): δ 1.82 (m, 14H), 2.83 (t, J = 7 Hz, 4H), 4.01 (t, J = 7 Hz, 4H), 6.20 (d, J = 13 Hz, 2H), 6.88 (d, J = 7 Hz, 2H), 7.29 (d, J = 7 Hz, 2H), 7.42 (t, J = 7 Hz, 2H), 7.73 (t, J = 7 Hz, 2H), 7.84 (d, J = 7 Hz, 2H), 8.04 (d, J = 7 Hz, 2H), 8.37 (d, J = 13 Hz, 2H); nir: λ max in methanol, 1013 nm.…”