$re = '/(?!\bi+\b)\b[dcmlxvi]+\b|(\bi+\.)/i';
$str = 'i ii. Both ix is i i. ii. i viii are roman numeral. mcmlxxxvii is wow year. Year is mmxvi. i.';
preg_match_all($re, $str, $matches, PREG_SET_ORDER, 0);
// Print the entire match result
var_dump($matches);
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php