Structure–property relationships of acylated asymmetric dithienophospholes

Phosphinine Lipids: A Successful Marriage between Electron‐Acceptor and Self‐Assembly Features

“…Table 2 shows the corresponding frontier orbital energies. Compared to the calculated LUMO energies of a related dithienophosphole oxide (E LUMO = À1.86 eV) [15] and DTDKP (E LUMO = À2.66 eV), [3] 2 shows an even lower LUMO energy level at E LUMO = À2.99 eV, thus supporting its improved electronaccepting capability, which is in good agreement with the electrochemical studies. The frontier orbitals (LUMO + 1, LUMO, HOMO, and HOMO-1) are depicted in Figure S5 in the Supporting Information.…”

A Simple and Effective Method of Determining Lewis Acidity by Using Fluorescence

“…Moreover, multinuclear NMR analysis supported an adduct formation between the phosphoryl group and the borane. 24,30 Most distinctively, the 31 atoms of the pentafluorophenyl rings at À133.2, À158.0, and À164.3 ppm, respectively, fully supporting a strong adduct formation. 31 The coordination of the borane to 1 was definitively proven via single-crystal X-ray crystallography (Figure 3).…”

Dithiazolo[5,4‐b:4′,5′‐d]phosphole: A Highly Luminescent Electron‐Accepting Building Block

“…However, in contrast to the P-oxo derivatives, the phosphorus lone pair in the trivalent species shows a large contribution to the LUMO. It is worth noting that, relative to the parent dithienophosphole oxide (E HOMO = À5.77, E LUMO = À1.86 eV), [23] the incorporation of nitrogen atoms into compound 2-O significantly lowers both HOMO (DE HOMO = À0.58 eV) and LUMO levels (DE LUMO = À0.35 eV), thus providing theoretical evidence for the dithiazolophosphole being a better electron-accepting building block for the design of n-type organic conjugated materials. Installation of the alkynyl group (2-O!4-O) leads to a pronounced stabilization of the LUMO (DE LUMO = À0.53 eV) and destabilization of the HOMO (DE HOMO = 0.26 eV) and, consequently, a smaller energy gap (DE g = À0.78 eV), which is consistent with the strong electron-accepting properties and the redshifted UV/Vis and emission spectra.…”