N-Oxide S–O chalcogen bonding in conjugated materials

Abstract

N-Oxide incorporation into thiazole-containing conjugated materials can have substantial effects on both the electronic and physical properties. A notably strong non-covalent S–O interaction is observed between the N-oxide and neighbouring sulfur.

Highly Efficient Mixed Conduction in N‐type Fused Small Molecule Semiconductors

“…[ 51 ] In addition, the natural bonding orbital (NBO) analysis was carried out to determine the contribution of non‐covalent interactions (Figure 1d and Table S1, Supporting Information). [ 52 ] From the analysis of the second order perturbation energies between the oxygen lone pairs (donor) and sulfur‐carbon antibonding orbital (acceptor), the stabilization energy provided by S–O interaction is calculated to be 5.46 kcal mol −1 . While the stabilization energy provided by H–O interaction is calculated to be 5.56 kcal mol −1 when analyzing the second‐order perturbation energies between the oxygen lone pairs (donor) and hydrogen‐carbon antibonding orbital (acceptor).…”

NaOH-Intercalated Iron Chalcogenides (Na1–xOH)Fe1–yX (X = Se, S): Ion-Exchange Synthesis and Physical Properties

“…27 14) Å, meaning that there may be chalcogen bonding in (Na 1−x OH)Fe 1−y Se. 61,62 Considering that the iron vacancy concentrations are about 20% in both (Na 1−x OH)Fe 1−y Se and the precursor K 0.8 Fe 1.6 Se 2 , there are few iron atoms filling the vacancies that accompany ion exchange. Similar structural features were observed for the S counterparts, except the iron vacancy concentration decreased from about 20% in K 0.8 Fe 1.6 S 2 to about 8% in (Na 1−x OH)Fe 1−y S, meaning that some iron ions may fill the vacancies during the ion-exchange process.…”

“…Similar large BVS values of Na can be found in YOVCOB (C 76 H 79 Cl 4 Co 6 N 12 NaO 14 ) and JODGAK (C 72 H 72 Cu 6 N 13 NaO 15 ). − The largest O–Na–O angles are 132.5(3)° for (Na 1– x OH)­Fe 1– y Se, suggesting the much higher degree of squashed distortion for the NaO 4 tetrahedra compared to the FeSe 4 tetrahedra. The shortest Se...O distance is 3.545(12) Å, and the shortest O...O distance is 3.216(14) Å, meaning that there may be chalcogen bonding in (Na 1– x OH)­Fe 1– y Se. , Considering that the iron vacancy concentrations are about 20% in both (Na 1– x OH)­Fe 1– y Se and the precursor K 0.8 Fe 1.6 Se 2 , there are few iron atoms filling the vacancies that accompany ion exchange. Similar structural features were observed for the S counterparts, except the iron vacancy concentration decreased from about 20% in K 0.8 Fe 1.6 S 2 to about 8% in (Na 1– x OH)­Fe 1– y S, meaning that some iron ions may fill the vacancies during the ion-exchange process.…”

A comparison of the positional effect of difluorination and the synergistic effect of siloxane-terminated side chains on benzodithiophene-based conjugated polymers for efficient photovoltaic application

“…For conjugated polymers composed of alternating donor and acceptor units, the tunable chemical structure of the building block can manipulate the optical absorption bands, molecular energy levels, as well as the three-dimensional molecular conformations. Many strategies have been developed to fine-tune the molecular structure of the polymer donors for high efficiency PSCs, such as terpolymerization of D-A polymers with different donor or acceptor building blocks as the third component, 4 the introduction of heteroatoms in the polymer backbone, [5][6][7][8][9][10][11][12][13][14][15] variation of the category or the length of the alkyl side chain [16][17][18] and introduction of electron-withdrawing substituents on 2-dimensional conjugated side chains. 19,20 In 2016, the 3,5-difluorobenzene group was introduced as the 2-dimensional conjugated side chain on the benzodithiophene (BDT) unit to compose a polymer donor (PTFBDT-BZS) by Bo et al for the first time.…”

“…6.93(6.57 AE 0.36) 17.75 26Si:IT-4F 1.00 1 30. 24.09 0.31(0.24 AE 0.07) 1.25a The average values in parentheses are obtained from over 15 devices.…”