4,4-Difluoro-8-(4-iodo-phen-yl)-1,3,5,7-tetra-methyl-3a-aza-4a-azonia-4-borata-s-indacene

Area of Science:

• Organic Chemistry
• Crystallography
• Materials Science

Background:

• Boron-dipyrromethene (BODIPY) dyes are known for their photophysical properties.
• Understanding the solid-state structure of BODIPY derivatives is essential for tuning their applications.
• The incorporation of heavy atoms like iodine can influence photophysical and structural characteristics.

Purpose of the Study:

• To synthesize and characterize a novel BODIPY derivative containing a 4-iodophenyl group.
• To elucidate the crystal structure of the title compound, C(19)H(18)BF(2)IN(2).
• To investigate the spatial arrangement of the BODIPY core relative to the iodophenyl moiety.

Main Methods:

• Single-crystal X-ray diffraction analysis was performed.
• The molecular structure and crystal packing were determined.
• Dihedral angles between key planes were precisely measured.

Main Results:

• The title compound, C(19)H(18)BF(2)IN(2), was successfully synthesized and structurally characterized.
• The BODIPY mean plane exhibited significant dihedral angles of 88.95° (with the F/B/F plane) and 78.21° (with the 4-iodophenyl plane).
• These angles indicate a near-perpendicular orientation between the BODIPY core and the iodophenyl substituent.

Conclusions:

• The determined dihedral angles provide critical insights into the solid-state conformation of this BODIPY derivative.
• The structural data is fundamental for predicting and optimizing the photophysical properties of related iodinated BODIPY compounds.
• This work contributes to the understanding of structure-property relationships in functional organic materials.