Synthesis, crystal structure and fluorescent properties of indolo[3,2-b]carbazole-based metal–organic coordination polymers

Chemistry and Properties of Indolocarbazoles

“…An ensuing Suzuki coupling with 1-bromo-2-(methylsulfinyl)benzene provided compound 299 in respectable yield, which eventually underwent a cyclization to the fused system 300 (Scheme 68). 298 Alkylation of the readily available 5,11-dihydro-6pentylindolo[3,2-b]carbazole 256 (301) with an excess of epichlorohydrin (used as reagent and cosolvent with THF) gave an excellent yield of the product 302 (Scheme 69), a monomer for construction of polymers via oxirane ring opening with thiophenol derivatives. 299 Likewise, exhaustive N-alkylation of 3,9-dibromo-6-hexyl-5,11-dihydroindolo[3,2-b]carbazole ( 258) obtained from 6-bromoindole and heptanal by following the same established protocol mentioned above 256 has been reported to take place in the presence of bromohexane and sodium hydride as the base in DMF solution, to provide a product displaying good solubility.…”

“…300 Alkylation has also been accomplished utilizing the Michael addition, as treatment of the parent indolo[3,2-b]carbazole 4 with butyl acrylate in the presence of DBU provided access to the diester 303, which could subsequently be converted to the dicarboxylic acid 304 in good overall yield (Scheme 70). 301 Several routes are available to brominated indolo[3,2b]carbazoles, which are useful building blocks for more advanced structures. Apart from the derivatives harboring bromine substituents inherited from the starting materials used in construction of the heterocyclic core, certain systems are accessible by introduction of bromine atoms into an already existing indolo[3,2-b]carbazole system at a later stage.…”

Singlet Fission, Polaron Formation, and Energy Transfer in Indolo[3,2-b]carbazole Thin Films and Single Crystals

“…In Figure a, the absorption spectrum of the ICZ solution shows three specific bands at 250–300, 300–350, and 350–420 nm ranges. The first two high-intensity bands are assigned to π–π* transitions peaking at 276, 321, and 338 nm; the latter low-intensity band at the 350–420 nm range is assigned to n−π* transitions with three humps at 366, 383, and 403 nm . The fluorescence emission spectrum of the ICZ solution contains a broad band with peak maxima at 415 and 439 nm and a small shoulder at 463 nm, which is the mirror image of the absorption spectrum at the 350–420 nm range.…”

“…The first two high-intensity bands are assigned to π−π* transitions peaking at 276, 321, and 338 nm; the latter low-intensity band at the 350−420 nm range is assigned to n−π* transitions with three humps at 366, 383, and 403 nm. 27 The fluorescence emission spectrum of the ICZ solution contains a broad band with peak maxima at 415 and 439 nm and a small shoulder at 463 nm, which is the mirror image of the absorption spectrum at the 350−420 nm range. It clearly exhibits the position of each vibrational level in the S 1 state of ICZ in DMF.…”

A Selenophene-Incorporated Metal–Organic Framework for Enhanced CO2 Uptake and Adsorption Selectivity

“…A porous coordination polymer [Zn 2 (bdc) 2 (dabco)] (dabco = 1,4-diazabicyclo[2.2.2]octane) is a prototypic compound of a bountiful MOF family with highly tunable structural features [ 26 , 27 , 28 , 29 , 30 ]. We have demonstrated that the incorporation of 2,5-thiophenedicarboxylate instead of the 1,4-benzenedicarboxylate into this MOF enhances both the CO 2 adsorption uptake and the CO 2 /N 2 adsorption selectivity of [Zn 2 (tdc) 2 (dabco)] by as much as 50%, compared with the original structure [Zn 2 (bdc) 2 (dabco)] at the same conditions [ 31 ].…”